Hydrochloric Acid → 1-(Benzyloxyimino-methyl)-4,4-dimethyl-cyclohexanecarboxylic acid

HRID 2055183Notes

Reaction equation

HRID 2055183 reaction equation
C[O:2][C:3]([C:5]1([CH:13]=[N:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][CH2:6]1)=[O:4].O.[OH-].[Li+].Cl>C1COCC1.O>[CH2:16]([O:15][N:14]=[CH:13][C:5]1([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][CH2:6]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 866064741-(Benzyloxyimino-methyl)-4,4-dimethyl-cyclohexanecarboxylic acid methyl ester

Product 1

HCID 866064751-(Benzyloxyimino-methyl)-4,4-dimethyl-cyclohexanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(benzyloxyimino-methyl)-4,4-dimethyl-cyclohexanecarboxylic acid methyl ester (1.83 g, 6.04 mmol) and lithium hydroxide monohydrate (2.53 g, 60.4 mmol) in THF (60 mL) and water (30 mL) was heated at 60° C. for 18 h. The reaction mixture was acidified to pH 5 with 3N aqueous HCl and was extracted with dichloromethane (50 mL×6). The combined organic layers were dried (MgSO4) and were evaporated in vacuo to yield the title compound as a pale yellow oil. (1.47 g, 84%). MH+290.

Workup

  1. extractionwas extracted with dichloromethane (50 mL×6)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-eaa712942cf049398097798156421513
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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