Isopropenyl acetate → HCID 53857451, compound

HRID 1833491Notes

Reaction equation

HRID 1833491 reaction equation
[CH3:1][C:2]([OH:11])([CH2:4][CH2:5][CH:6]=[CH:7][C:8]([CH3:10])=[CH2:9])[CH3:3].[C:12](OC(C)=C)(=[O:14])[CH3:13]>CCCCCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:12]([O:11][C:2]([CH3:1])([CH2:4][CH2:5][CH:6]=[CH:7][C:8]([CH3:10])=[CH2:9])[CH3:3])(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 7916Isopropenyl acetateHCID 53748541HCID 53748541, compound

Product 1

HCID 53857451HCID 53857451, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8058HexaneSolvent

Procedure

6.7 g of 2,7-dimethyl-5,7-octadien-2-ol, 13 g of isopropenyl acetate and 0.1 g of p-toluenesulphonic acid are heated at reflux for 3 hours in a three-necked flask provided with a thermometer, stirrer and reflux condenser. The mixture is taken up in 100 ml of hexane and washed with a saturated sodium bicarbonate solution and with water. The solvent is distilled off and the residue fractionally distilled. There are obtained 3.4 g of 2,7-dimethyl-5,7-octadien-2-ol acetate of boiling point 60° C/0.2 mm Hg; nD20 = 1.4675; d420 = 0.9077. The yield is 40% of theory.

Workup

  1. temperatureat reflux for 3 hours in a three-necked flask
  2. customprovided with a thermometer, stirrer
  3. temperaturereflux condenser
  4. washwashed with a saturated sodium bicarbonate solution and with water
  5. distillationThe solvent is distilled off
  6. distillationthe residue fractionally distilled

Sources & evidence

ORD record
ord-129600186b8b43b1bfe57f75b2a45fd6
Source dataset
uspto-grants-1978_01
Patent number
US04066710

Reaction notes

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