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

HRID 354524Notes

Reaction equation

HRID 354524 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-cyclohexyl-cyclohexanol in 750 ml of N,N-dimethylaniline. The mixture is then allowed to come to room temperature, after which 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 on a 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-cyclohexyl-cyclohexane 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 on a 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-17873164b51c4ef2804cf4fa49058b25
Source dataset
uspto-grants-1983_03
Patent number
US04375428

Reaction notes

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