Benzyl 2-hydroxyacetate → HCID 86679579, compound

HRID 1776620Notes

Reaction equation

HRID 1776620 reaction equation
[OH:1][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23](Cl)(=[O:25])=[O:24])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>C(Cl)Cl.Cl>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23]([O:1][CH2:2][C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])(=[O:24])=[O:25])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

5

Reactant 2

HCID 561337Benzyl 2-hydroxyacetateHCID 27341833,4-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 86679579HCID 86679579, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Benzyl 2-hydroxyacetate (211 mg, 1.268 mmol) was dissolved in DCM (10 ml). TEA (0.265 ml, 1.901 mmol) and 3,4-dimethoxybenzene-1-sulfonyl chloride (300 mg, 1.268 mmol) were added, and the reaction was stirred at RT for 3 hours to achieve completion. The reaction mixture was diluted with HCl 1N and extracted with DCM. The organic phase was washed with HCl 1N and Na2CO3 sat. sol., dried over Na2SO4 and concentrated under vacuum to give benzyl 2-(3,4-dimethoxyphenylsulfonyloxy)acetate (400 mg, 86% yield).

Workup

  1. extractionextracted with DCM
  2. washThe organic phase was washed with HCl 1N and Na2CO3 sat. sol.
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b6fe16e2e80d465c814f9fdff57b6b7d
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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