Glycolic Acid → HCID 86758807, compound

HRID 1635086Notes

Reaction equation

HRID 1635086 reaction equation
[OH:1][C@@H:2]([C:13]([O:26][CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(O)(=O)[CH2:29][OH:30]>ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:20]1([C:13]2([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C@@H:2]([C:3]([O:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:4])[O:1][C:29](=[O:30])[CH2:27][O:26]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 757Glycolic AcidHCID 86758808HCID 86758808, compound

Product 1

HCID 86758807HCID 86758807, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

38 g (100 mmol) of the benzyl (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionate were added to 9.8 g (130 mmol) of glycolic acid, and the mixture was stirred with 300 mg of anhydrous para-toluenesulfonic acid at 70° C. on a rotary evaporator under reduced pressure for 20 minutes. The content of the flask was taken up in dichloromethane, the acid was separated off using sodium hydrogen sulfate solution, the organic phase was separated off and dried and the solvent was distilled off. The residue was recrystallized from ether, and 21 g (54 mmol) of product were isolated.

Workup

  1. customthe acid was separated off
  2. customthe organic phase was separated off
  3. customdried
  4. distillationthe solvent was distilled off
  5. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-4f5cab216291464e82a8c6e40e17461d
Source dataset
uspto-grants-2003_01
Patent number
US06509341B1

Reaction notes

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