Acetic Anhydride → 2-Acetyloxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid phenylmethyl ester

HRID 1613057Notes

Reaction equation

HRID 1613057 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:49])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:24]=3[O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[C:12]([CH2:45][CH2:46][CH3:47])[C:11]=2[OH:48])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:50](OC(=O)C)(=[O:52])[CH3:51]>N1C=CC=CC=1>[C:1]1([CH2:7][O:8][C:9](=[O:49])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:24]=3[O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[C:12]([CH2:45][CH2:46][CH3:47])[C:11]=2[O:48][C:50](=[O:52])[CH3:51])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 149863322-Hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid phenylmethyl ester

Product 1

HCID 149863332-Acetyloxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.15 g of 2-hydroxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid phenylmethyl ester in 15 mL of pyridine and 15 mL of acetic anhydride was stirred and heated at 50° for 15 hours. The reaction mixture was concentrated on the oil pump. The residue was dissolved in ethyl acetate and the solution was washed with sodium bicarbonate solution, dried and concentrated under reduced pressure to give 1.03 g of 2-acetyloxy-4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-3-propylbenzoic acid phenylmethyl ester as an oil.

Workup

  1. temperatureheated at 50° for 15 hours
  2. concentrationThe reaction mixture was concentrated on the oil pump
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4c7b387329c47fca34b3ee9aff8bd18
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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