Sulfuric Acid → 2-[4-Benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-hydroxyacetic acid

HRID 367343Notes

Reaction equation

HRID 367343 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:21])[C:16]([O:18]CC)=[O:17])=[CH:11][C:10]=1[CH2:22][CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].S(=O)(=O)(O)O>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:21])[C:16]([OH:18])=[O:17])=[CH:11][C:10]=1[CH2:22][CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 23287822Ethyl 2-[4-benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-hydroxyacetate

Product 1

HCID 232878162-[4-Benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-hydroxyacetic acidYield 94.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-[4-benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-hydroxyacetate (39.7 g) was suspended in 40 ml of ethanol, 57 ml of 2 N aqueous sodium hydroxide solution was added to the suspension with stirring under ice-cooling, and the mixture was subjected to 1 hour of reaction at room temperature. Then, 57 ml of 2 N aqueous sulfuric acid solution was added to the reaction solution with stirring under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was washed with water and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was evaporated under reduced pressure to give 35.1 g of 2-[4-benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-hydroxyacetic acid in an oily form.

Workup

  1. temperaturecooling
  2. customthe mixture was subjected to 1 hour of reaction at room temperature
  3. stirringwith stirring under ice-
  4. temperaturecooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThereafter, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9da2023c93a24659984c816e6853207f
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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