3-Methoxyphenyl benzoate

Preparation from 2-iodo-3-methoxyphenyl benzoate by rearrangement on treatment with n-butyllithium in a mixture of ethyl ether, hexane and tetrahydrofuran at -70° for 2 h, followed by treatment with saturated aqueous ammonium chloride (51%) [58]. 

Preparation by hydrolysis of 4-acetyl-3-methoxyphenyl acetate with boiling 10% sodium hydroxide solution (58%) [2791] or 4-acetyl-3-methoxyphenyl benzoate with potassium hydroxide in refluxing methanol (85%) [2792]. 

There are also some trends when looking at the main chain flexibility. Table II demonstrates that when the main chain flexibility decreases from cyanobiphenyl containing polymethacrylates to polysiloxanes, not only does the Tg drop, but the isotropization temperature increases. However, the trend is the opposite when the mesogen is methoxyphenyl benzoate (18). Therefore, this effect of the main chain flexibility is still ambiguous. 

Table 5 Mesomorphic behavior of the isomeric carbosilane dendrimers bearing methoxyphenyl benzoate (B) and anisic acid derivative (D) mesogens...

Synonyms 4-Allyl-2-methoxyphenyl benzoate Benzoyl eugenol Eugenol benzoate... 

Also obtained by Fries rearrangement of p-methoxyphenyl benzoate with titanium tetrachloride without solvent at 120° for 1 h (20-35%) [679],... 

Also obtained by Fries rearrangement of m-methoxyphenyl benzoate in the presence of trifluoro-methanesulfonic acid in tetrachloroethane at 170° for 24 h in a sealed tube (78%) [37]. 

Preparation by reaction of p-methoxyben-zoyl chloride with p-methoxyphenyl benzoate in the presence of stannic chloride in nitromethane at 20° for 2 days, followed by saponification of the m-keto ester so obtained— the 2,4 -dimethoxy-5-(4-meth-oxybenzoyloxy)benzophenone (73%)—with sodium hydroxide in refluxing methanol for 1 h (quantitative yield) [679]. oil [679] b.p. (NA) H NMR [679], IR [679], UV [679],... 

Also obtained by saponification of 4-acetyl-2-methoxyphenyl benzoate with boiling aqueous sodium hydroxide (56%) [2800],... 

The complete interpretation of these data is unfortunately difficult since these polymers form different types of mesophases Polymers with cyanobiphenyl and pyrimidine groups form smectic mesophases, and polymers with methoxyphenyl-benzoate groups form a nematic mesophase (although this difference in the types of mesophases perhaps also determines the type of change in T ). The effect of DP on Tci should also not be excluded in this case. 

When Cl and MeO substituents are attached to the phenolic ring, the PFR may result in displacement of those substituents by the acyl moiety. An example of chlorine displacement has been given in Section I, whereas Scheme 10 shows the case of 2-methoxy-4-methylphenyl benzoate (26), where the reaction mixture contains 2-hydroxy-5-methylbenzophenone (27), a product of methoxy substim-tion [37]. Hageman also reported the substitution of MeO by acetyl in the photolysis of 4-methoxyphenyl acetate and related esters [32]. 

Name 4-Methoxyphenyl-4-[4-(allyloxy) phenyl] benzoate Structure ... 

Bis[4-methylphenyl] ditellurium, bis[4-methoxyphenyl] ditellurium, and bis[4-ethoxy-phenyl] ditellurium, but not diphenyl or bis[2-naphthyl] ditcllurium, reacted with 2-(phenyliodonio)-benzoates producing compounds with two vicinal aryltelluro substituents in the aromatic ring. The reactions are postulated to proceed via the thermally generated singlet benzyne and concerted addition of the diaryl ditellurium compounds. 

When bis[4-methoxyphenyl] selenide telluride was heated with 5-methyl-2-(phenyl-iodonio)benzoate, an inseparable mixture of equal amounts of the two isomeric [4 -methoxyphenylseleno)-5-methylphenyl] 4-methoxyphenyl tellurium products was obtained. Molecules with two aryltelluro or two arylseleno groups in the molecule were not detected2. 

Bis[4-methoxyphenyl] tellurium, obtained from 4-methoxybenzene and tellurium tetrachloride and reduction of the resultant bis[4-methoxyphenyl] tellurium dichloride, was converted to methyl 4-methoxybenzoate in 99% yield1. Methyl benzoate was similarly obtained from diphenyl tellurium in yields higher than 90%. These reactions can be carried out with catalytic amounts of palladium(II) chloride when copper(II) chloride is used as an oxidant1. 

Similar studies were conducted with 1-phenylethyl benzoate derivatives labeled with, sO (radioactive) or, 70 (NMR active) carbonyl groups. Substituents in the alkyl groups and in the leaving group affect both the rates and the nature of the carbenium ion intermediates. For example, 1-phenylethyl p-nitrobenzoate undergoes solvolysis [Eq. (19)] at 60° C in 70% aqueous acetone 30,000 times slower than the corresponding l-(p-methoxyphenyl)ethyl derivative [54]. 

BzBr, Zn(OTf)2, CICH2CH2CI, 10-30 min, 9-98% yield. The benzoate is formed from TBDMS, Bn, and anomeric 4-methoxyphenyl ethers. ... 

MDDB 4-Methoxyphenyl[(((4-dipropargylamino)phenyl)oxy)dodecanyl]oxy] benzoate PMDDB Poly 4-Methoxyphenyl[(((4-dipropargylamino)phenyl)oxy)dodecanyl]oxy benzoate... 

Composition The main component is eugenol (ca. 70%y, typical accompanying compounds are linalool (2%), cinnamaldehyde (2%), safrole (2%), eugenyl acetate (4-ally 1-2-methoxyphenyl acetate, C12H14O3, Mr 206.24) (2%), and benzyl benzoate (see benzoic acid) (4%). 

An acid chloride functionalized liquid crystalline material was tried to bond to the silanol group in silica. The direct reaction does not seem to be successful also, a spacer with a substituted dichlorodimethyl silane is not successful. The reaction scheme is shown in Figure 16.8. However, a separation performance is observed rather by deposition than by bonding of the liquid crystals. The liquid crystalline materials used in this study was based on cholesteric moieties. It is suspected that the reaction failed because of the large size of the cholesteryl group. In another study, dimeth-ylchlorosilane was added to the allyl group of 4-methoxyphenyl-4-allyloxy benzoate. This intermediate could be bonded to silica. Several other routes to fix liquid crystalline moieties on silica have been reviewed. ... 

Methoxynaphthalene, 223 p-Methoxyphenol, 99 4-Methoxyphenyl-4-allyloxy benzoate, 537 Methoxyphenylisocyanate, 306 4-Methoxyphenylsulfonyl chloride, 253 Methyl-(4-anilino-phenyl) sulfide, 187, 188 A -(a-Methylbenzyloxy)-2,2,6,6-tetramethylpiperidine, 41 p-Methylbenzyltrimethylammonium hydroxide, 70... 

To a solution of NaOEt prepared from 0.11 g sodium (4.7 mmol) and 10 mL absolute ethanol, cooled in an ice bath, was added in rapid succession 0.88 g methyl 2-chloro-6-hydroxybenzoate (4.7 mmol) and a solution of 1.14 g A-4-methoxyphenylbenzimidyl chloride (4.7 mmol) in 30 mL dry ether. The reaction mixture was shaken vigorously, whereupon a precipitate of sodium chloride began to form. The mixture was allowed to stand at room temperature for 48 h, the solvent was evaporated, and the residue was diluted with water. The resulting oily solid was removed by extraction with ether, the ethereal solution was dried, and the ether was distilled. The crude imido ester was heated in a nitrogen atmosphere at 210-215 C for 70 min, then dissolved in 10.8 mL ethanol the alcoholic solution was diluted with 5.4 mL water and 5.4 mL of a 1 M ethanolic sodium ethoxide. The solution was refluxed for 1.5 h, the alcohol was evaporated on a steam bath, and the aqueous solution was acidified with dilute HCl. The dark oil that formed was separated by decantation, and the crude benzoate of the substituted anthranilic acid was dissolved in 22 mL ethanol. A solution of 7.2 g sodium hydroxide in 7.2 mL water was added, and the mixture was refluxed for 1 h. The alcohol was evaporated, and the solution was then acidified. The brown solid was extracted exhaustively with boiling water to remove the benzoic acid, and the remaining brown solid was recrystallized from aqueous ethanol. The yellow needle-like crystals of A-(4 -methoxyphenyl)-6-chloroanthranilic acid, in a total amount of 0.36 g, was obtained, in a yield of 27.7%, m.p., 139.5-140.5°C (dec). 

Hydroxy 2-methyl 1-phenyl 1-propanone 4-(p-Hydroxyphenyl)-2-butanone Isoeugenol Isopropyl benzoate 1 -(p-Methoxyphenyl)-2-propanone 4-Methyl benzyl acetate a-Methylbenzyl acetate -a-Methylbenzyl acetate Methylbenzyl acetate, mixed o-, m-, p-Methyl 3-phenylpropionate... 

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