Acetic Anhydride → HCID 68481881, compound

HRID 1873455Notes

Reaction equation

HRID 1873455 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH2:5][CH2:4][C:3]1([CH2:11][OH:12])[CH:9]=[CH2:10].C(N(CC)CC)C.[CH3:20][C:21](OC(C)=O)=[O:22]>CN(C1C=CN=CC=1)C.CCOCC>[C:21]([O:12][CH2:11][C:3]1([CH:9]=[CH2:10])[CH2:4][CH2:5][C:6]([CH3:8])=[CH:7][CH:2]1[CH3:1])(=[O:22])[CH3:20]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68481936HCID 68481936, compound

Product 1

HCID 68481881HCID 68481881, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (2,4-dimethyl-1-vinylcyclohex-3-enyl)methanol (3.50 g, 21.1 mmol), triethylamine (3.83 g, 38 mmol) and a catalytic amount of DMAP in Et2O (30 ml) was added Ac2O (3.22 g, 31.6 mmol). The mixture was stirred for 5 h, poured on water and extracted with Et2O. The combined organic layers were washed with water and brine, dried and evaporated in vacuo. The residue was distilled bulb-to-bulb to yield (2,4-dimethyl-1-vinylcyclohex-3-enyl)methyl acetate (3.81 g, 86%) as a colorless oil.

Workup

  1. additionpoured on water
  2. extractionextracted with Et2O
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. customevaporated in vacuo
  6. distillationThe residue was distilled bulb-to-bulb

Sources & evidence

ORD record
ord-6baba3c808474ae083b68f3d623421b4
Source dataset
uspto-grants-2012_11
Patent number
US08304380B2

Reaction notes

Loading…