4-[[2-(Cyclohexyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester → 4-[[2-(Cyclohexyloxy)ethyl]oxy]-alphaoxobenzeneacetic acid

HRID 2225700Notes

Reaction equation

HRID 2225700 reaction equation
C[O:2][C:3](=[O:22])[C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:7][CH:6]=1>CO.[OH-].[Na+]>[CH:15]1([O:14][CH2:13][CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([C:4](=[O:21])[C:3]([OH:22])=[O:2])=[CH:10][CH:9]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

4

Reactant 1

HCID 543210414-[[2-(Cyclohexyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 190043524-[[2-(Cyclohexyloxy)ethyl]oxy]-alphaoxobenzeneacetic acidYield 89.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-[[2-(cyclohexyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.7 g) in methanol (10 mL) and 0.5N sodium hydroxide (7 mL) was treated as in Example 19. Extraction with diethyl ether provided material which was crystallized from diethyl ether-hexane to give 0.6 g of colorless 4-[[2-(cyclohexyloxy)ethyl]oxy]-alphaoxobenzeneacetic acid, mp 96°-98° C.

Workup

  1. additionwas treated as in Example 19
  2. extractionExtraction with diethyl ether provided material which
  3. customwas crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-90b957c3af2c469c9d3603aee62c589e
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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