(Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate → (Z)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadienyl)-2-pentenyl acetate

HRID 1195478Notes

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: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

Conditions

Temperature: -10 °C

Procedure

A solution of (Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate (0.98 g) in acetonitrile (15 ml) was treated dropwise at -20° C. with a solution of ceric ammonium nitrate (4.1 g) in water (15 ml). After 15 minutes the mixture was warmed to -10° C and left at this temperature for 1 hour. The mixture was diluted with ice-water and extracted twice with methylene chloride. The extracts were washed with water, dried and chromatographed on silica gel with hexane/ethyl acetate 95:5, yielding 0.67 g of (Z)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadienyl)-2-pentenyl acetate as a pale yellow oil.

Workup

extractionextracted twice with methylene chloride
washThe extracts were washed with water
customdried
customchromatographed on silica gel with hexane/ethyl acetate 95:5

Sources & evidence

ORD record: ord-ba9765f56afc446187891225b81cf41f
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05110955

Reaction notes

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