Ether Petrolic

Dimethylphenylsilyl lithium (1 mmol, above THF solution) was added to copper(i) iodide (0.5 mmol) at — 23 °C, and the mixture was stirred at this temperature for 4h. The enone (0.75-0.5mmol) was then added, and stirring was continued at —23 °C for 0.5 h. The mixture was then poured on to ice(25 g)/HCl(5 ml), and extracted with chloroform (3 x 25 ml). The combined extracts were filtered, washed with HCI (25ml, 3m), water (25 ml), saturated sodium hydrogen carbonate solution (25 ml) and water (25 ml), and dried. Concentration and purification by preparative t.l.c. (eluting solvent 3 7 ether petrol) gave the /J-silylketone (40-99%). 

The submitters purified the product by the following procedure. The residual pale yellow solid is dissolved in 50 ml of diethyl ether and the remaining solid is filtered off (Note 16). The filtrate is concentrated to a volume of ca. 25 mL, and the solution is allowed to crystallize at 0°C. Once crystallization begins, 50 mL of petroleum ether is added in two portions over 10 hr, and then crystallization is allowed to proceed overnight at 0°C. The white solid is collected by filtration and washed with a mixture of 3 1 petroleum ether-diethyl ether to afford 3.8 g of 4. Chromatographic purification of the mother liquor (5.5 x 18 cm of DSH silica gel 40-63 mm, elution with 1 L of petroleum ether/ethyl acetate 4 1 followed by 1.5 L of 3 1 petroleum ether-ethyl acetate) gives 2.5 g of 4 as a pale yellow solid. All the material is combined and recrystallized from diethyl ether/petrol as above to yield 5.2 g (47%) of 4 in two crops. 

The remaining solution was diluted with DCM (2 ml), and m-chloroperbenzoic acid (mCPBA) (0.30 g, 2.0 mmol) was added portionwise. After stirring at RT for 40 h, the mixture was extracted with DCM and washed successively with aqueous sodium sulfite solution, aqueous sodium bicarbonate solution and water, dried (MgS04) and evaporated in vacuum. Column chromatography (45-70% ether-petrol, gradient elution) of the residue afforded the title epoxides (3aa,6a,7a,7aa)-6,7-epoxy-3a,6,7,7a-tetrahydrobenzo[d]-l,3-dioxol-2-one (73 mg, 47%) mp 87°-89°C and (3aa,6p,7p,7aa)-6,7-epoxy-3a,6,7,7a-... 

Tetrafluoroboric acid-diethyl ether complex (catalytic amount) was added to a stirred solution of epoxide (+/-)-(3aa,6a,7a,7aa)-6,7-epoxy-3a,6,7,7a-tetrahydrobenzo[d]-l,3-dioxol-2-one (32 mg, 0.2 mmol) and (R)-(+)-sec-phenethyl alcohol (0.048 ml, 0.4 mmol) in DCM at RT under argon. After 30 min, water was added and the mixture extracted with DCM (3 times). The combined organic phase was dried (MgS04) and evaporated in vacuum. Column chromatography (30-75% ether-petrol, gradient elution) of the residue afforded the alcohols [3aR-[3aa,4a,5p(R),7aa]-3a,4,5,7a-tetrahydro-4-hydroxy-5-(l-phenylethoxy)benzo[d]-l,3-dioxol-2-one and [3aS-[3aa,4a,5P(R),7aa]-3a,4,5,7a-tetrahydro-4-hydroxy-5-(l-phenylethoxy)benzo[d]-l,3-dioxol-2-one. (37 mg, 67%) as a thick oil and a 1 1 mixture of diastereomers. Subsequent HIPLC (l -Dynamax 83,123-6 column 6% isopropanol-petrol, 15 ml/min) effected separation of the diastereomers. Less polar [3aR-[3aa,4a,5p(R),7aa]-3a,4,5,7a-tetrahydro-4-hydroxy-5-(l-phenylethoxy)benzo[d]-l,3-dioxol-2-one had retention time 16.3 min [a]D2° +90.1° (c 1.1, CHCI3). 

Camphorsulphonic acid monohydrate (catalytic amount) was added to a stirred solution of [lR-[la,2a,3 3,4a(R),5a,6a)-3-benzyloxy-5,6-epoxy-4-(l-phenylethoxy)cyclohexane-l,2-diol (0.321 g, 0.9 mmol) in 2,2-dimethoxypropane (10 ml) at RT under argon. After 16 h, the mixture was poured into DCM and washed with aqueous sodium bicarbonate solution and water. The aqueous layers were reextracted with DCM and the combined organic extracts dried (MgS04) and evaporated in vacuum column chromatography (50% ether-petrol) of the residue afforded the title epoxy acetonide (0.317 g, 89%) as needles, m.p. 114°-115°C (recrystallized from ether-petrol) [a]D2°+134.1° (c 1.00, CHCI3). 

Tetraethyllead is a transparent colourless liquid in small concentrations its vapours have a sweetish fruity smell in large concentrations it has an unpleasant odour. Tetraethyllead boils at 200 °C (with decomposition) d420 = 1.6524 nD20= 1.5198. It does not dissolve in water but can be easily dissolved in alcohols, diethyl ether, petrol, acetone and other organic solvents. 

Phosphorus trichloride is a colourless transparent motile liquid (the boiling point is 76 °C) it fumes in air. It mixes with diethyl ether, petrol, chloroform, carbon disulfide and dichloroethane in all ratios It can be easily destroyed with water, acids and alcohols. Phosphorus trichloride vapours hydrolyse even in humid air. 

Carotenoid analysis was determined spectrophotometrically using methods from Sandmann.36 Under dim light, 20 mL of methanol containing 6% KOH was added to 40 mg of leaf material and heated to 60°C for 20 min. The methanol extract was poured into a separatory funnel with 10 mL of 10% diethyl ether (petroleum ether). 10 mL of saturated NaCI solution was added. The upper layer was collected, and the lower one was re-extracted with another 10 mL of diethyl ether/petrol. Total carotenoid content was determined in the combined upper layers by determining volume and measuring optical absorbance at 445 and 550... 

Oils, fats, and waxes are all insoluble in water most of them, however, dissolve in organic solvents such as chloroform, ether, petrol, benzene, or the chlorinated hydrocarbons. They also form emulsions of varying degrees of stability when shaken with water containing soap or other emulsifying agents. Fats and related substances can be removed from textiles by three methods ... 

C). Slightly oJ in water misc with alcohol chloroform, ether, petrol ether. Keep tightly closed. LDW orally in rat 0.7 g/kg (Smyth, Carpenter). 

Formiria QjHuOsNRR, R and R are fatty acid groups Properties Nearly wh. to yel. or bm. waxy mass or thick fluid, nutlike odor, bland taste sol. in chloroform, ether, petrol, ether, min. oils, fatty acids, hydrocarbon and chlorinated soivs. insol. but swells in water and salt sol ns. insol. in veg. oils dens. 1.0305 (24/4 C) HLB 8.0 acid no. 15-30 iodine no. 95 sapqn. no. 196 nonionic Toxicology May cause bronchoconstriction in people with asthma TSCA listed... 

Pmperiies Coloriess clear liq. ether-like sweet odor sol. in water, acetone, benzene, CCI, ethyl ether, petrol, ether, methanol misc. with oxygenated soivs. m.w. 90.14 dens. 0.919 m.p. -96.7 C b.p. 120 C flash pt. (CC) 32 C... 

Definition Semisolid mixture of hydrocarbons obtained from petroleum Properties YIsh. to It. amber or wh. semisolid, unctuous mass pract. odorless and tasteless sol. in benzene, chloroform, ether, petrol, ether, oils pract. insol. in water insol. in alcohol dens. 0.820-0.865 (60/25 C) m.p. 38-54 C soften, pt. 65-70 C ref. index 1.460-1.474 (60 C) Toxicoiogy LD50 (IP, mouse) > 50 g/kg can cause allergic skin reactions... 

Properties Colorless to wh. crystals or powd., odorless, tasteless sol. in hot alcohol, benzene, chloroform, carbon disulfide, chlorinated and aromatic soivs. pract. insol. in cold alcohol, ether, petrol, ether insol. in water m.w. 891.45 dens. 0.943 (65 C) m.p. 71.6 C ref. index 1.4385 (80 C) nonionic Toxicology No known toxicity TSCA listed Precaution Combustible... 

Properties Colorless or pale straw clear oily liq., nearly odorless, bland taste si. sol. in alcohol misc. with chloroform, ether, petrol, spirit insol. in water sp.gr. 0.910-0.923 acid no. 1 max. iodine no. 90-115 sapon. no. 185-195 ref. index 1.4635-1.4655(40 C)... 

Properties Purple hexagonal prisms, red leaflets sol. in carbon disulfide, benzene, chloroform, veg. oils mod. sol. in ether, petrol, ether, oils pract. insol. in water m.w. 536.89 m.p. 178-179 C Toxicology Nontoxic on skin massive doses may cause yellowing of the skin mutagen TSCA... 

Empirical C16H32 Formula CH3(CH2)i3CH=CH2 Properties Colorless liq., mild hydrocarbon odor sol. in alcohol, ether, petrol, and coal-tar soivs. si. sol. in water dens. 0.785 b.p. 518-554 F m.p. 37 F ref. index 1.4420 flash pt. (Seta) 272 F Toxicology Irritating to skin and eyes low acute inhalation toxicity low acute ingestion toxicity but ingestion may cause vomiting, aspiration of vomitus... 

CAS 143-07-7 EINECS/ELINCS 205-582-1 FEMA 2614 INS570 E570 Synonyms Dodecanoic acid n-Dodecanoic acid Dodecoic acid Duodecylic acid Laurostearic acid 1-Undecanecarboxylic acid Classification Fatty acid Empirical C12H24O2 Formula CH3(CH2)ioCOOH Properties Colorless needles si. bay oil odor sol. in benzene, chloroform, alcohol, ether, petrol, ether insol. in water m.w. 200.36 dens. 0.833 vapor pressure 1 mm (121 C) m.p. 44 C b.p. 225 C (100 mm) ref. index 1.4323 (45 C)... 

Properties Colorless transparent oily liq., odorless, tasteless insol. in water, alcohol sol. in benzene, chloroform, ether, petrol, ether, carbon disulfide, volatile oils dens. 0.83-0.86 (light), 0.875-0.905 (heavy) flash pt. (OC) 444 F surf. tens. < 35 dynes/cm... 

Properties Off-wh. cryst., powd., or lumps disagreeable sulfurous mushroom odor very sol. in ethanol, ether, petrol, ether sparingly sol. in... 

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