Ethyl [4-(3-oxomorpholin-4-yl)phenyl]acetate → 4-(3-Oxomorpholin-4-yl)phenylacetic acid

HRID 602347Notes

Reaction equation

HRID 602347 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17]CC)=[O:16])=[CH:10][CH:9]=1>[OH-].[Na+].C(O)C>[O:1]=[C:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 58691263Ethyl [4-(3-oxomorpholin-4-yl)phenyl]acetate

Product 1

HCID 586912414-(3-Oxomorpholin-4-yl)phenylacetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

20.2 g (76.8 mmol) of ethyl [4-(3-oxomorpholin-4-yl)phenyl]acetate are dissolved in a solution of 3.37 g of sodium hydroxide in 40 ml of ethanol, and the reaction solution is stirred at room temperature for 18 hours. The reaction mixture is evaporated, and the residue is dissolved in water and acidified to a pH of 3 using 1N hydrochloric acid. The mixture is extracted with ethyl acetate, and the organic phase is dried over sodium sulfate and evaporated, giving 4-(3-oxomorpholin-4-yl)phenylacetic acid as a yellowish solid; ESI 236.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in water
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-170d3c7a97ec4276bbece135aae11fd5
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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