Acetic Anhydride → (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate

HRID 1195469Notes

Reaction equation

HRID 1195469 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

Reactant 2

HCID 7918Acetic AnhydrideHCID 15837167(E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-penten-1-ol

Product 1

HCID 19819048(E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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.

Workup

  1. extractionThe mixture was extracted with ether
  2. washThe combined extracts were washed with water
  3. customdried
  4. customthe residue obtained
  5. customwas purified on silica gel with hexane/ethyl acetate (95:5)

Sources & evidence

ORD record
ord-6fcc848ac9ba4bd1929152ce31dc782b
Source dataset
uspto-grants-1992_05
Patent number
US05110955

Reaction notes

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