Acetic Anhydride → HCID 178448090, compound

HRID 1730612Notes

Reaction equation

HRID 1730612 reaction equation
[C:1]([C@@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)([CH3:3])=[CH2:2].[C:12](OC(=O)C)(=[O:14])[CH3:13]>N1C=CC=CC=1>[C:12]([O:11][CH2:10][C@H:7]1[CH2:8][CH2:9][C@@H:4]([C:1]([CH3:3])=[CH2:2])[CH2:5][CH2:6]1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178448083HCID 178448083, compound

Product 1

HCID 178448090HCID 178448090, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.9 g of cis-4-isopropenyl-cyclohexylmethanol, 50 ml of acetic anhydride and 20 ml of pyridine were kept overnight at room temperature. The reaction mixture was then poured onto crushed ice and extracted with ether. The organic layer was successively washed with a 2N solution of Na2CO3, HCl at 10% in water and finally with a saturated aqueous NaCl solution. After the usual treatments of drying and evaporation, the fractional distillation of the obtained residue yielded 3.2 g (65%) of cis-4-isopropenyl-cyclohexylmethyl acetate, bp 105° - 108°/10 Torr.

Workup

  1. additionThe reaction mixture was then poured
  2. customonto crushed ice
  3. extractionextracted with ether
  4. washThe organic layer was successively washed with a 2N solution of Na2CO3, HCl at 10% in water and finally with a saturated aqueous NaCl solution
  5. customAfter the usual treatments of drying
  6. customevaporation
  7. distillationthe fractional distillation of the obtained residue

Sources & evidence

ORD record
ord-0c00408ba26c4e54820b8978cf6571a9
Source dataset
uspto-grants-1976_11
Patent number
US03993604

Reaction notes

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