Sodium Hydroxide → 6-(4-Acetyl-3-hydroxy-2-propylphenoxy)-6-(4-benzylphenyl)hexanoic acid

HRID 543216Notes

Reaction equation

HRID 543216 reaction equation
[C:1]([C:4]1[CH:33]=[CH:32][C:7]([O:8][CH:9]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:21][CH:20]=2)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[C:6]([CH2:34][CH2:35][CH3:36])[C:5]=1[OH:37])(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([C:4]1[CH:33]=[CH:32][C:7]([O:8][CH:9]([C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:23][CH:24]=2)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[C:6]([CH2:34][CH2:35][CH3:36])[C:5]=1[OH:37])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13881965Ethyl 6-(4-acetyl-3-hydroxy-2-propylphenoxy)-6-(4-benzylphenyl)hexanoate

Product 1

HCID 138819666-(4-Acetyl-3-hydroxy-2-propylphenoxy)-6-(4-benzylphenyl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.5 g. of ethyl 6-(4-acetyl-3-hydroxy-2-propylphenoxy)-6-(4-benzylphenyl)hexanoate in 40 ml. of 1N sodium hydroxide and 20 ml. of ethanol was stirred for 24 hours. The reaction was diluted with 100 ml. of water, and was extracted with hexane and ethyl acetate. The aqueous layer was acidified with hydrochloric acid and extracted twice with ethyl acetate. The ethyl acetate layers were combined, dried over sodium sulfate, and evaporated in vacuo yielding 1.83 g. of the title product.

Workup

  1. additionThe reaction was diluted with 100 ml
  2. extractionof water, and was extracted with hexane and ethyl acetate
  3. extractionextracted twice with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customyielding 1.83 g

Sources & evidence

ORD record
ord-f4e6f63cc4e640e599c02ef1b80fb7ac
Source dataset
uspto-grants-1987_04
Patent number
US04661505

Reaction notes

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