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

HRID 1787164Notes

Reaction equation

HRID 1787164 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-2d45c89bf97c4e4384b04b3d4a5a80aa
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

Loading…