Acetic Anhydride → (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15]/[C:16](/[CH3:20])=[CH:17]/[CH2:18][OH:19].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([O:19][CH2:18]/[CH:17]=[C:16](\[CH3:20])/[CH2:15][CH2:14][C:4]1[C:5]([CH3:13])=[C:6]([O:11][CH3:12])[C:7]([CH3:10])=[C:8]([CH3:9])[C:3]=1[O:2][CH3:1])(=[O:23])[CH3:22]Participants
4
Procedure
A solution of 4.17 g (15 mmol) of (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-penten-1-ol in pyridine (10 ml) and acetic anhydride (2 ml) was stirred at room temperature for 5 hours and thereafter poured into ice-cold 2N hydrochloric acid solution. The mixture was extracted with ether. The combined extracts were washed with water, dried and freed from solvent; the residue obtained was purified on silica gel with hexane/ethyl acetate (95:5), yielding 3.8 g of (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate as a colourless oil.