Water → 3-Benzyloxy-2,2-bis(benzyloxymethyl)propionic acid

HRID 1162944Notes

Reaction equation

HRID 1162944 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]([O:21][CH2:22][C:23]([CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([CH2:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:24][OH:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CC(C)=O>[CH2:37]([O:36][CH2:35][C:23]([CH2:22][O:21][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([CH2:26][O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:24]([OH:3])=[O:25])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12082528TetrabenzylpentaerythritolHCID 131709961Jones' reagent

Product 1

HCID 575579373-Benzyloxy-2,2-bis(benzyloxymethyl)propionic acidYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A Jones reagent (0.984 mmol) was added to 5 mL of a solution of 3-benzyloxy-2,2-bis(benzyloxymethyl)propan-1-ol (200 mg, 0.492 mmol) obtained in the Step A in acetone under ice-cooling, and the mixture was stirred at room temperature for one hour. Water was added to the mixture, followed by extraction with ethyl acetate. The extract was washed with saturated saline and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 3-benzyloxy-2,2-bis(benzyloxymethyl)propionic acid (206 mg, 100%) as a colorless solid.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0ebee8715a6144dfa800fe96897bfb4f
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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