Methanol → HCID 14794002, compound

HRID 329485Notes

Reaction equation

HRID 329485 reaction equation
C([CH:6]1[CH:11]([CH2:12][CH2:13][C:14]([O:17][CH3:18])([CH3:16])[CH3:15])[CH2:10][CH2:9][CH2:8][C:7]1=[O:19])(OCC)=O.[OH-].[K+].CO>O>[CH3:18][O:17][C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][CH:11]1[CH2:10][CH2:9][CH2:8][C:7](=[O:19])[CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 14794005HCID 14794005, compound

Product 1

HCID 14794002HCID 14794002, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Crude 2-carbethoxy-3-(3-methoxy-3-methylbut-1-yl)cyclohexanone (7.0 g) of example 17 was added to a mixture of potassium hydroxide (3.0 g), methanol (50 mL) and water (50 mL) and heated at reflux 4.5 hours. The cooled mixture was extracted with hexane, the extracts were dried (Na2SO4) and concentrated to an oil which was purified by bulb to bulb distillation, airbath temperature 175° C., 0.1 mm Hg to yield 3-(3-methoxy-3-methylbut-1-yl)cyclohexanone (1.0 g); NMR(CDCl3)δ1.2(s,6H), 1.2-1.5(m,5H), 1.6-1.8(m,2H), 1.9-2.1(m,3H), 2.2-2.4(m,3H), 3.2(s,3H); IR(neat) 2970, 2950, 1720, 1460, 1370, 1230, 1090 cm-1 ; MS(m/e) 41, 55, 73, 110, 133, 151, 183, 184.

Workup

  1. temperatureheated
  2. temperatureat reflux 4.5 hours
  3. extractionThe cooled mixture was extracted with hexane
  4. dry with materialthe extracts were dried (Na2SO4)
  5. concentrationconcentrated to an oil which
  6. distillationwas purified by bulb to bulb distillation, airbath temperature 175° C., 0.1 mm Hg

Sources & evidence

ORD record
ord-0c57de15ff2d490e9836bee545ba8e89
Source dataset
uspto-grants-1990_01
Patent number
US04891447

Reaction notes

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