p-Toluenesulfonic acid → 1,1-Dimethoxycyclohexane

HRID 1609385Notes

Reaction equation

HRID 1609385 reaction equation
[C:1]1(=O)[CH2:6][CH2:5]C[CH2:3][CH2:2]1.[CH:8](OC)([O:11][CH3:12])[O:9][CH3:10].C(O)C(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:10][O:9][C:8]1([O:11][CH3:12])[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6560IsobutanolHCID 7967CyclohexanoneHCID 9005Trimethyl orthoformate

Product 1

HCID 136161,1-Dimethoxycyclohexane

Procedure

Cyclohexanone dimethyl ketal (CHMK) was prepared as described in Example 1 from 1 mol of cyclohexanone and trimethyl orthoformate. 370.6 g of isobutanol (2-methyl-1-propanol, 5.0 mols) were added, and the transketalization was then carried out under reflux while the sump temperature was gradually increased from 110° to 160° C. After a running time of 2 hours, another 0.4 g of p-toluenesulfonic acid was added. The low-boiling-point components, i.e. methyl formate, methanol and a small amount of isobutyl formate, were removed by distillation under reflux (ratio 1:5 to 1:2) over the course of 4 hours.

Workup

  1. temperatureunder reflux while the sump temperature
  2. temperaturewas gradually increased from 110° to 160° C
  3. customThe low-boiling-point components, i.e. methyl formate, methanol and a small amount of isobutyl formate, were removed by distillation
  4. temperatureunder reflux (ratio 1:5 to 1:2) over the course of 4 hours

Sources & evidence

ORD record
ord-7494e292c8174cdd8b0415f471985ec2
Source dataset
uspto-grants-1995_03
Patent number
US05399778

Reaction notes

Loading…