Hydrochloric Acid → 1-{[(Benzyloxy)imino]methyl}cyclohexane-1-carboxylic acid

HRID 2055173Notes

Reaction equation

HRID 2055173 reaction equation
C[O:2][C:3]([C:5]1([CH:11]=[N:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].Cl>C1COCC1.CO.O>[CH2:14]([O:13][N:12]=[CH:11][C:5]1([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866064721-(Benzyloxyimino-methyl)-cyclohexanecarboxylic acid methyl ester

Product 1

HCID 714169841-{[(Benzyloxy)imino]methyl}cyclohexane-1-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(benzyloxyimino-methyl)-cyclohexanecarboxylic acid methyl ester (1.75 g, 6.36 mmol) and sodium hydroxide (0.76 g, 19.1 mmol) in THF (10 mL), methanol (10 mL) and water (5 mL) was stirred at room temperature for 40 h. The reaction mixture was acidified to pH 4 with 3N aqueous HCl and was extracted with EtOAc (50 mL×2). The combined organic layers were dried (MgSO4) and were evaporated in vacuo to yield the title compound as a yellow oil. (1.59 g, 96%). MH+262.

Workup

  1. extractionwas extracted with EtOAc (50 mL×2)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-04b7a45c2f4d4074bcb33fd989c8b218
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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