Acetyl chloride → 2-Methyl[1,1'-bi(cyclohexane)]-2-yl acetate

HRID 1277527Notes

Reaction equation

HRID 1277527 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(OC(=O)C)(=O)C.[CH3:12][C:13]1([OH:25])[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C)C1C=CC=CC=1.CCOCC>[C:1]([O:25][C:13]1([CH3:12])[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 20507686HCID 20507686, compound

Product 1

HCID 205076852-Methyl[1,1'-bi(cyclohexane)]-2-yl acetate

Reagents, catalysts & solvents 2

HCID 949N,N-DimethylanilineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 360 ml of acetyl chloride and 153 ml of acetic acid anhydride is added dropwise at 0° C., whilst stirring, to a solution of 576 g of crude 1-methyl-2-cyclohexylcyclohexanol in 750 ml of N,N-dimethylaniline. The mixture is then allowed to come to room temperature, after which it is heated to 40° C. for 36 hours. Thereafter, the reaction mixture is poured onto ice and diluted with 1 liter of ether, and the organic phase is separated off and concentrated ona Rotavapor apparatus. The residue is then taken up in 2 liters of ether and the solution is washed with three times 200 ml of cold 2-N HCl and then with saturated bicarbonate solution and water until neutral, and is dried with anhydrous MgSO4 and evaporated in vacuo. 646 g of crude 1-acetoxy-1-methyl-2-cyclohexylcyclohexane are obtained.

Workup

  1. additionis added dropwise at 0° C.
  2. customto come to room temperature
  3. additionThereafter, the reaction mixture is poured onto ice
  4. customthe organic phase is separated off
  5. concentrationconcentrated ona Rotavapor apparatus
  6. washthe solution is washed with three times 200 ml of cold 2-N HCl
  7. dry with materialwith saturated bicarbonate solution and water until neutral, and is dried with anhydrous MgSO4
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-26a9ca3b5bdc460d9c1b85e404b3c302
Source dataset
uspto-grants-1981_07
Patent number
US04277618

Reaction notes

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