Sodium Dichromate → 1589-19-1

HRID 1383706Notes

Reaction equation

HRID 1383706 reaction equation
[CH2:1]([CH:16]1[CH2:21][CH2:20][CH2:19][CH:18]([OH:22])[CH2:17]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>C(O)(=O)C.O>[CH2:1]([CH:16]1[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[CH2:17]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 25408Sodium DichromateHCID 11695283HCID 11695283, compound

Product 1

HCID 45234491589-19-1

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 25 g (80 mmol) of 3-pentadecylcyclohexanol in 190 ml of glacial acetic acid was cooled to about 0° C., with stirring, and a solution of 8.33 g (31.8 mmol) of sodium dichromate in 14 ml of glacial acetic acid and 5 ml of water was added dropwise over 4.5 hours at a temperature below 10° C. The reaction mixture was heated to 60° C. for one hour and vacuum stripped to remove acetic acid. The residue was diluted with water and extracted with ethyl acetate. The extract was washed with aqueous sodium bicarbonate solution and water and dried over sodium sulfate. Upon vacuum stripping of the solvent, the desired 3-pentadecylcyclohexanone was obtained as a waxy solid, m.p. 41° C. The yield was 23 g (92% of theoretical).

Workup

  1. customto remove acetic acid
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with aqueous sodium bicarbonate solution and water
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-9b49169e2704413d83c9b33b1f36da3e
Source dataset
uspto-grants-2001_07
Patent number
US06255439B1

Reaction notes

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