1- Hydroxy hexane

SYNS AMYLCARBINOL CAPROYL ALCOHOL EPAL 6 FEMA No. 2567 HEX.3NOL n-HEXANOL 1-HEXANOL HEXYL ALCOHOL 1-HYDROXY-HEXANE PENTYLCARBINOL... 

Synonyms hexyl alcohol pentylcarbinol amylcarbinol caproyl alcohol 1-hydroxy-hexane... 

Condensation of butanol has been carried out on alkaline earth metal oxides at 273 K (13,121). This condensation reaction yields 2-ethyl-3-hydroxy-hexanal as a main product other products, such as 2-ethyl-2-hexenal (arising from the dehydration of 2-ethyl-3-hydroxy-hexanal), n-butyl-K-butyrate (arising from the Tishchenko reaction of butyraldehyde), and 2-ethyl-3-hydroxy- -hexyl butyrate (arising from the Tishchenko reaction of 2-ethyl-3-hydroxy-hexanal), are also formed (Scheme 12). 

The order of activity per unit surface area was equal to that in the case of selfcondensation of acetone and in agreement with the order of basicity of the solids, namely, SrO > CaO > MgO. However, the authors found that the rate-determining step for aldol condensation of n-butyraldehyde is the a-hydrogen abstraction by the active sites, which are the surface ions. The differences in rate-determining step and active sites in the condensation of butyraldehyde and aldol condensation of the acetone were attributed to differences in acidity of the a-hydrogen in the two molecules. CaO was slightly more active than MgO at 273 K after a reaction time of 1 h, maximum conversions of 41% were observed with selectivities to 2-ethyl-3-hydroxy-hexanal and to the corresponding Tishchenko reaction product (2-ethyl-3-hydroxy- -hexyl butyrate) of 39.8 and 56.9%, respectively. 

R = C4H9 2-Hydroxy-hexan-thiophosphonsiiure 43°/0 R = CSHU 2-Hydroxy-heptan-thiophosphonsdure 45%... 

Commercial Preparation.—The commercial method for preparing oxalic acid, up to a few years ago, was by the oxidation of sawdust or sugar. In practice sawdust was oxidized by heating it with fused alkali by which process the alkali salt of oxalic acid was obtained. When sugar, or similar organic substances, like cellulose, are oxidized the reaction may be illustrated by the oxidation of the hexa-hydroxy hexane, or mannitol, as follows ... 

Hexyl - (2) -hypochlorit Tetrachlor- 6 - Chlor-2-hydroxy-hexan 56 1,5... 

Both chiral compounds have been prepared by enantioselective reduction of ethyl-5-oxohexanoate 71 and 5-oxohexanenitrile 72 by Pichia methanolica SC 16116. Reaction yields of 80%-90% and more than 95% EEs were obtained for each chiral compound. In an alternate approach, the enzymatic resolution of racemic 5-hydroxy-hexane nitrile 73 by enzymatic succinylation was demonstrated using immobilized lipase PS-30 to obtain (S)-5-hydroxyhexanenitrile 69 in 35% yield (maximum yield is 50%). (S)-5-Acetoxy-hexanenitrile 74 was prepared by enantioselective enzymatic hydrolysis of racemic 5-acetoxyhexanenitrile 75 by Candida antarctica lipase. A reaction yield of 42% and an EE of more than 99% were obtained [96]. 

Acetylformoin (3-hydroxy-hexane-2,4,5-trione CH3-CO-CH(OH)-CO-CO-CH3) is a suspected major product of the OH initiated oxidation of 3-hexene-2,5-dione, itself a product of the OH initiated oxidation of p-xylene. This compound has been synthesised in its isomeric enediol form 3-hexene-3,4-diol-2,5-dione. The rate coefficients for the reaction with OH radicals was found to be (2.7 0.7) X 10 ° cm s" The residual FTIR spectrum of its OH initiated photooxidation was found to be identical to that obtained from the OH initiated oxidation of 3-hexene-2,5-dione, the major product has been tentatively identified as hexane-3,3-diol-2,4,5-trione (CH3 CO-C(OH)2-CO-CO-CH3). These results suggest that acetylformoin readily enolises and then rapidly reacts with OH radicals to give products of the type observed for the OH initiated oxidation of 3-hexene-3,4-diol-2,5-dione. 

A A Dimethylamino)phenol. 4-Hydroxy-Ai,A/-dimethylaniline (20) forms large rhombic crystals from diethyl ether—hexane or diethyl ether—ligroin. It forms a salt with sulfuric acid, mp 208—210°C (187). 

Syn 3-(EthyltHloniethyl)-4-hydroxy-6-pt)enyl-2-hexanone (4) and anti (5) To ethanethiol (10 0 mg 0 17 mmol) in THF (2 mL) was added 1 54 M n butyltittnum m hexane (0 11 mL) at 0 C under Ar Stannous triflate (69 0 mg 017 nvnol) was added and alter 20 mm the mocture was cooled to 4S°C Methyl vinyl Ketone 1 (118 mg 1 98 mmol) m THF (1 5 mL) was added followed by 3 phenyiptopanal 3 350 mg 2 61 mmol) m THF (1 S mL) Alter 12 h aq cilnc acid was added and the organic material extracted with OHjClj The resxlue after evaporation was dissolved in MeOH and treated with citric acxt After 30 min stimng, the mixture was quenched with pH 7 phosphate buffer extracted with CH2CI2, the solvent evaporated and the residue chromatographed to afford 336 mg ot 4 (75%), syn anti (90 10)... 

Hydroxy-2-methylazobenzene [1435-88-7] M 212.2, m 100-101°, pKesi 9.5. Crystd from hexane. 

Hydroxy-3-methylgIutaric acid (Meglutol) [503-49-1J M 162.1, m 99-102 , 108-109 , 100 , pKestd) 4.0, pK star -O. Recrystd from diethyl ether/hexane and dried under vac at 60° for Ih. 

A solution of 1 g of the ethyleneketal of the trione in 40 ml of methanol is treated with 0.2 g of sodium borohydride and the mixture is stirred at 20° for 2 hr. Slow drop wise addition of water precipitates the reaction product as crystals. These are filtered, washed with water and dried, to give 1.02 g of hydroxy ketone, which after crystallization from methylene dichloride-hexane has mp 182-184° (reported 184-186°) -23° (CHCI3). 

P,17P-Dihydroxyestr-4-en-3-one 1-acetate. The 6-hydroxy compound is removed from the column with 15-17% acetone. Recrystallization of the crude product (1.92 g) from acetone-hexane gives 1.25 g of crystals melting at 165-166° and 0.13 g melting at 162-164° (12.1% yield). When the analytical sample was prepared from the same solvent mixture, the melting point rose to 192-193° (Lit 166° 189-190°) [a] -59.5° (CHCI3) 2, 236 m/i (fi 14,500). 

Hydroxy-4-fluoroestr-4-en-3-one is obtained by rechromatography on Florisil of the combined material of the late eluates from the isolation of the 4,4-difIuoride and the mother liquor from the recrystallization of the latter. Elutions with 1 1 methylene dichloride-ether yield 0.41 g of crude monofluoride mp 143-146°. Recrystallization from hexane-acetone affords 0.29 g of pure monofluoride mp 147-148° [aJo 49° (CHCI3) X 248 m i ( , 15,000). 

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