Acetic Anhydride → 3-Cyclohexene-1-methanol, alpha,4,6,6-tetramethyl-, 1-acetate

HRID 1449319Notes

Reaction equation

HRID 1449319 reaction equation
[CH3:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH:5]([CH:10]([OH:12])[CH3:11])[CH2:4][CH:3]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>O>[CH3:1][C:2]1[CH2:7][C:6]([CH3:8])([CH3:9])[CH:5]([CH:10]([O:12][C:13](=[O:15])[CH3:14])[CH3:11])[CH2:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19901996HCID 19901996, compound

Product 1

HCID 1127023-Cyclohexene-1-methanol, alpha,4,6,6-tetramethyl-, 1-acetateYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 liter flask, provided with a mechanical stirrer, a heater and a reflux condenser fitted with a calcium chloride drying tube, is charged with 190.8 g of 1,5,5-trimethyl-4-(1-hydroxyethyl)-cyclohex-1-ene and 173.8 g of acetic anhydride. The mixture is brought to 100° for 4 hours. After cooling, the mixture is immersed in 250 ml of water and extracted with 3 times 100 ml of benzene. The extract is then washed once with 100 ml of water, twice with 100 ml of a 9% solution of sodium bicarbonate and twice more with 100 ml of water. The solvent is distilled off on a water bath, finally, under a pressure of 30 mm of mercury; the crude ester is distilled in a 500 ml three-necked flask fitted with a 1 meter adiabatic column filled with unoxidisable 4×4 mm particles, under a vacuum of 0.5 mm of mercury. 197 g of 1,5,5-trimethyl-4-(1 -acetoxyethyl)-cyclohex-1-ene (81.3%) are obtained having the following physical properties:

Workup

  1. customA 1 liter flask, provided with a mechanical stirrer
  2. customa heater and a reflux condenser fitted with a calcium chloride drying tube
  3. temperatureAfter cooling
  4. extractionextracted with 3 times 100 ml of benzene
  5. washThe extract is then washed once with 100 ml of water, twice with 100 ml of a 9% solution of sodium bicarbonate and twice more with 100 ml of water
  6. distillationThe solvent is distilled off on a water bath
  7. distillationthe crude ester is distilled in a 500 ml three-necked flask
  8. customfitted with a 1 meter adiabatic column
  9. additionfilled with unoxidisable 4×4 mm particles, under a vacuum of 0.5 mm of mercury

Sources & evidence

ORD record
ord-74d34628f12b444888108a95d661006c
Source dataset
uspto-grants-1980_02
Patent number
US04190561

Reaction notes

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