Water → HCID 20379140, compound

HRID 2051599Notes

Reaction equation

HRID 2051599 reaction equation
[CH3:1][C:2]([CH:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1)([CH2:5][CH3:6])[CH2:3][CH3:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].O.S(=O)(=O)(O)O>C1C=CC=CC=1>[CH3:1][C:2]([CH:7]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]1)([CH2:5][CH3:6])[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 25408Sodium DichromateHCID 20379124HCID 20379124, compound

Product 1

HCID 20379140HCID 20379140, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

The 4-(3-methylpent-3-yl)cyclohexanol (350 g, 1.9 mol) prepared above was added slowly over a 3 hour period to a stirring solution of sodium dichromate (614 g, 2.06 mol), water (3.0 liters) and 98% sulfuric acid (526 g) while maintaining the batch temperature at 50°-55° C. Upon completion of the addition, the mixture was stirred an additional hour at 50° C. The reaction mixture was cooled and three liters of benzene was added. The layers were separated and the organic layer washed with one liter portions of water until a neutral pH was indicated. The solvent was removed on a rotary evaporator. Distillation of the residual oil under vacuum gave the desired 4-(3-methylpent-3-yl)cyclohexanone: 274 g, 79% theory; bp 105° C. (0.5 mm); mol wt 182 (ms); nmr, 0.75 (3H, s, methyl, 0.8 (6H, t, J=7, methyls), 1.15-2.0 (9H, m, CH, CH2), 2.15-2.5 (4H, m, Hα to carbonyl); ir, 2980, 2890, 1720, 1465, 1390, 1170 cm-1.

Workup

  1. temperaturewhile maintaining the batch temperature at 50°-55° C
  2. additionUpon completion of the addition
  3. temperatureThe reaction mixture was cooled
  4. customThe layers were separated
  5. washthe organic layer washed with one liter portions of water until a neutral pH
  6. customThe solvent was removed on a rotary evaporator
  7. distillationDistillation of the residual oil under vacuum

Sources & evidence

ORD record
ord-9a68aec065f84f90ad27de20326c5db4
Source dataset
uspto-grants-1980_01
Patent number
US04181631

Reaction notes

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