1-Isopropyl-4-(2-methyl-3-(4-methylphenoxy)propene-1-yl)benzene → 2-(1-(4-Isopropylphenyl)-2-methyl-2-propenyl)-4-methylphenol

HRID 2376299Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([CH3:21])[CH2:12][O:13]C2C=CC(C)=CC=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>CN(C)C1C=CC=CC=1.C(OC(C)C)(C)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([C:11]2[CH:21]=[C:4]([CH3:5])[CH:1]=[CH:2][C:12]=2[OH:13])[C:7]([CH3:8])=[CH2:6])=[CH:8][CH:9]=1)([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 215 °C

Procedure

A solution of 1-isopropyl-4-(2-methyl-3-(4-methylphenoxy)propene-1-yl)benzene obtained in Reference Example 87 (8.2 g, 29.2 mmol) in N,N-dimethylaniline (50 mL) was stirred under argon atmosphere at 215° C. for 16 hours. After cooling, the reaction mixture was diluted with diisopropyl ether, washed with 5 N hydrochloric acid and water, dried over magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 7.80 g (yield 95%) of the title compound. Oily matter.

Workup

temperatureAfter cooling
washwashed with 5 N hydrochloric acid and water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-8a5ee606e9b14d4996680d592d37d90b
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465815B2

Reaction notes

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