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

HRID 1195477Notes

Reaction equation

HRID 1195477 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][O:9][C:10]1[C:15]([CH3:16])=[C:14]([CH3:17])[C:13]([O:18][CH3:19])=[C:12]([CH3:20])[C:11]=1[CH2:21][CH2:22]/[C:23](/C)=[CH:24]\CO>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:5]([O:4][CH2:1]/[CH:2]=[C:23](/[CH3:24])\[CH2:22][CH2:21][C:11]1[C:12]([CH3:20])=[C:13]([O:18][CH3:19])[C:14]([CH3:17])=[C:15]([CH3:16])[C:10]=1[O:9][CH3:8])(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 22843765(Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-penten-1-ol

Product 1

HCID 86745749(Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.2 ml) was dissolved at 0° C. in pyridine (10 ml) together with (Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-penten-1-ol (0.39 g; 1.4 mmol). A spatula tip of 4-dimethylaminopyridine was added and the reaction mixture was left at 0° C. for 20 minutes. Thereafter, the mixture was poured into 150 ml of ice-cold 2N hydrochloric acid and extracted with ether. The extracts were washed with water, dried briefly and freed from solvent, yielding 0.39 g of (Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate as an almost colourless oil.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with water
  3. customdried briefly

Sources & evidence

ORD record
ord-e9c358e553d949e198fbad1554333732
Source dataset
uspto-grants-1992_05
Patent number
US05110955

Reaction notes

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