(E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate → (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl acetate

HRID 1195470Notes

Reaction equation

HRID 1195470 reaction equation
[C:1]([O:4][CH2:5]/[CH:6]=[C:7](\[CH3:23])/[CH2:8][CH2:9][C:10]1[C:15]([CH3:16])=[C:14]([O:17]C)[C:13]([CH3:19])=[C:12]([CH3:20])[C:11]=1[O:21]C)(=[O:3])[CH3:2]>C(#N)C.O.C(Cl)(Cl)Cl>[C:1]([O:4][CH2:5]/[CH:6]=[C:7](\[CH3:23])/[CH2:8][CH2:9][C:10]1[C:11](=[O:21])[C:12]([CH3:20])=[C:13]([CH3:19])[C:14](=[O:17])[C:15]=1[CH3:16])(=[O:3])[CH3:2]

Participants

5

Reactant 1

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

Product 1

HCID 19819053(E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl acetateYield 93.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 3.83 g (12 mmol) of (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate in acetonitrile (50 ml) was treated dropwise at 0° C. with a solution of ceric ammonium nitrate (16.4 g; 30 mmol) in water (50 ml). After completion of the addition the mixture was stirred for a further 20 minutes and diluted with water and chloroform. The organic phase was separated, washed with water, dried and concentrated to a yellow oil, yielding (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl acetate (3.27 g).

Workup

  1. additionAfter completion of the addition the mixture
  2. customThe organic phase was separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated to a yellow oil

Sources & evidence

ORD record
ord-120c2451ddd3442a864c2ff6a56951a6
Source dataset
uspto-grants-1992_05
Patent number
US05110955

Reaction notes

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