N,N-Diethylaniline → 2-Allyl-3,5-dimethylphenol

HRID 2376354Notes

Reaction equation

HRID 2376354 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[CH:6]=1)C=C.C(OCC)(=O)C.C(N(CC)[C:22]1[CH:27]=CC=C[CH:23]=1)C>>[CH2:27]([C:10]1[C:9]([CH3:11])=[CH:8][C:7]([CH3:12])=[CH:6][C:5]=1[OH:4])[CH:22]=[CH2:23]

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 8857Ethyl AcetateHCID 257959Allyl 3,5-dimethylphenyl ether

Product 1

HCID 2596542-Allyl-3,5-dimethylphenolYield 94%

Conditions

Temperature
210 °C

Procedure

A solution of 1-(allyloxy)-3,5-dimethylbenzene obtained in Reference Example 214 (1.0 g, 6.2 mmol) in N,N-diethylaniline (4 mL) was stirred under argon atmosphere at 210° C. for 5 hours. To the reaction solution was added ethyl acetate, and the mixture was washed with hydrochloric acid and a saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 7:3) to obtain 938 mg (yield 94%) of the title compound. Oily matter.

Workup

  1. washthe mixture was washed with hydrochloric acid
  2. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 7:3)

Sources & evidence

ORD record
ord-3df74d03c5d6434193664eef25b6c333
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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