Acetic Anhydride → HCID 68481881, compound

HRID 2361567Notes

Reaction equation

HRID 2361567 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-e141f7e00e184fe59b959e06e81d061f
Source dataset
uspto-grants-2014_04
Patent number
US08691746B2

Reaction notes

Loading…