Benzyl 3-benzyloxy-2-chloro-4-methanesulfonylbenzoate → 3-Benzyloxy-2-chloro-4-methanesulfonylbenzoic acid

HRID 704301

Reaction equation

HRID 704301 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([Cl:29])=[C:11]([CH:22]=[CH:23][C:24]=1[S:25]([CH3:28])(=[O:27])=[O:26])[C:12]([O:14]CC1C=CC=CC=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Na]>C(O)C>[CH2:1]([O:8][C:9]1[C:10]([Cl:29])=[C:11]([CH:22]=[CH:23][C:24]=1[S:25]([CH3:28])(=[O:27])=[O:26])[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15132921Benzyl 3-benzyloxy-2-chloro-4-methanesulfonylbenzoateHCID 23872008Sodium hydrochloride

Product 1

HCID 151329223-Benzyloxy-2-chloro-4-methanesulfonylbenzoic acidYield 50.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 g of benzyl 3-benzyloxy-2-chloro-4-methanesulfonylbenzoate was put into 50 ml of ethanol, and 25 ml of an aqueous solution containing 1 g of sodium hydrochloride was added thereto. The mixture was stirred at room temperature for 30 minutes. Then, ethanol was distilled off, and water was added to the residue. The mixture was washed with chloroform. The aqueous layer was acidified with concentrated hydrochloric acid and then extracted with chloroform. The extract was dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain a crude product of the above identified compound. The crude product was washed with ethanol-isopropyl ether to obtain 1.0 g of the desired product.

Workup

  1. additionwas added
  2. distillationThen, ethanol was distilled off
  3. additionwater was added to the residue
  4. washThe mixture was washed with chloroform
  5. extractionextracted with chloroform
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. distillationThen, the solvent was distilled off
  8. customto obtain a crude product of the
  9. washThe crude product was washed with ethanol-isopropyl ether

Sources & evidence

ORD record
ord-c89a35b6bf6d45938e6bcdedbc3f29a3
Source dataset
uspto-grants-1991_01
Patent number
US04986845

Linked notes

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