Formic Acid → 3-Cyclohexene-1-methanol, .alpha.,4,6,6-tetramethyl-, 1-formate

HRID 1449322Notes

Reaction equation

HRID 1449322 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.[CH:13](O)=[O:14]>O>[CH3:1][C:2]1[CH2:7][C:6]([CH3:8])([CH3:9])[CH:5]([CH:10]([O:12][CH:13]=[O:14])[CH3:11])[CH2:4][CH:3]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 19901996HCID 19901996, compound

Product 1

HCID 1127033-Cyclohexene-1-methanol, .alpha.,4,6,6-tetramethyl-, 1-formateYield 47.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20.0 g of 1,5,5-trimethyl-4-(1-hydroxyethyl)-cyclohex-1-ene are introduced into a 1 liter three-necked flask provided with a mechanical stirrer, a heater, a dropping funnel and a reflux condenser fitted with a calcium chloride drying tube. 273 g of formic acid are then added in the course of 1/2 hour, whilst maintaining the temperature of the reaction mixture between 0° and 5°. After the end of the addition, the temperature of the composition is maintained at 5°. The composition is then slowly heated over 2 hours to 20°-25°. The mixture is then poured into 200 ml of water and extracted with benzene. The combined benzene extracts are washed successively with water, a solution of sodium bicarbonate and, finally, with water again. After distillation of the solvent over a water bath, the crude ester is distilled under a pressure of 0.05 mm of mercury. 11.0 g of 1,5,5-trimethyl-4-(1-formyloxyethyl)-cyclohex-1-ene are obtained, having the following physical constants:

Workup

  1. customprovided with a mechanical stirrer
  2. customa heater, a dropping funnel and a reflux condenser fitted with a calcium chloride drying tube
  3. temperaturewhilst maintaining the temperature of the reaction mixture between 0° and 5°
  4. additionAfter the end of the addition
  5. temperaturethe temperature of the composition is maintained at 5°
  6. temperatureThe composition is then slowly heated over 2 hours to 20°-25°
  7. extractionextracted with benzene
  8. washThe combined benzene extracts are washed successively with water
  9. distillationAfter distillation of the solvent over a water bath
  10. distillationthe crude ester is distilled under a pressure of 0.05 mm of mercury

Sources & evidence

ORD record
ord-6c78465b6d004f26bd51f6fd5fe5e66c
Source dataset
uspto-grants-1980_02
Patent number
US04190561

Reaction notes

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