Sodium Chromate → 4-(3,5-Dichlorophenylmethyl)cyclohexanone

HRID 727165

Reaction equation

HRID 727165 reaction equation
[Cr]([O-])([O-])(=O)=O.[Na+].[Na+].[Cl:8][C:9]1[CH:10]=[C:11]([CH2:16][CH:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)[CH:12]=[C:13]([Cl:15])[CH:14]=1>C(OCC)C>[Cl:8][C:9]1[CH:10]=[C:11]([CH2:16][CH:17]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[CH:12]=[C:13]([Cl:15])[CH:14]=1

Participants

4

Reactant 2

HCID 24488Sodium ChromateHCID 197052214-(3,5-Dichlorophenylmethyl)cyclohexanol

Product 1

HCID 197052684-(3,5-Dichlorophenylmethyl)cyclohexanoneYield 36.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of chromic acid was prepared using 5.6 grams of sodium dichromate, 16.8 mL of water, 4.1 mL of concentrated sulfuric acid, and additional water to provide 28 mL of solution. The sodium chromate solution was cooled to 0° C. and was added dropwise to a stirred, cold (0° C.) solution of 7.3 grams (0.028 mole) of 4-(3,5-dichlorophenylmethyl)cyclohexanol in 15 mL of diethyl ether. The complete addition required about 5 minutes. Upon completion of addition, the reaction mixture was stirred for 5 minutes and then was extracted with diethyl ether. The ether extract was washed with an aqueous solution saturated with sodium bicarbonate, then with water. The organic layer was concentrated under reduced pressure, yielding 2.6 grams of 4-(3,5-dichlorophenylmethyl)cyclohexanone.

Workup

  1. additionThe complete addition required about 5 minutes
  2. additionUpon completion of addition
  3. extractionwas extracted with diethyl ether
  4. extractionThe ether extract
  5. washwas washed with an aqueous solution saturated with sodium bicarbonate
  6. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3d06a9f5a66428e9a8fed0fd0be5ceb
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Linked notes

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