Sodium Hydroxide → HCID 24262708, compound

HRID 1776621Notes

Reaction equation

HRID 1776621 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([O:14][CH2:15][C:16]([O:18]CC2C=CC=CC=2)=[O:17])(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+]>CO.Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([O:14][CH2:15][C:16]([OH:18])=[O:17])(=[O:12])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86679579HCID 86679579, compound

Product 1

HCID 24262708HCID 24262708, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Benzyl 2-(3,4-dimethoxyphenylsulfonyloxy)acetate (400 mg, 1.092 mmol) was dissolved in MeOH (5 ml). NaOH 1M (2 ml) was added, and the reaction was stirred at RT for 6 hours to achieve completion. The reaction mixture was diluted with HCl 1N and extracted with EtOAc. The organic phase was washed with HCl 1N and brine, dried over Na2SO4 and concentrated under vacuum. The crude product was triturated in petroleum ether to give 2-(3,4-dimethoxyphenylsulfonyloxy)acetic acid (250 mg, 83% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with HCl 1N and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe crude product was triturated in petroleum ether

Sources & evidence

ORD record
ord-5af2d1e2b6334565a3d4f01005f4c011
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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