Hydrochloric Acid → Phenol, 2,3,5-trimethyl-6-(2-methyl-2-propenyl)-

HRID 2063778Notes

Reaction equation

HRID 2063778 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9]CC(C)=C)[C:3]=1[CH3:14].C(N(CC)[C:18]1[CH:23]=CC=C[CH:19]=1)C.Cl.[C:27](OCC)(=O)C>>[CH3:27][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([CH3:1])=[C:3]([CH2:14][C:18]([CH3:23])=[CH2:19])[C:4]=1[OH:9]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7061N,N-DiethylanilineHCID 8857Ethyl AcetateHCID 11830229Benzene, 1,2,5-trimethyl-3-[(2-methyl-2-propenyl)oxy]-

Product 1

HCID 10655310Phenol, 2,3,5-trimethyl-6-(2-methyl-2-propenyl)-Yield 85%

Conditions

Temperature
225 °C

Procedure

A mixture of 1,2,5-trimethyl-3-[(2-methylprop-2-en-1-yl)oxy]benzene (33.6 g, 177 mmol) synthesized in Reference Example 1 and N,N-diethylaniline (100 mL) was stirred under argon atmosphere at 220 to 230° C. for 11 hours. After cooled to room temperature, the reaction solution was distributed using ethyl acetate and 1N hydrochloric acid. The organic layer was washed with 1N hydrochloric acid and saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 40:1 to 9:1) to give 28.6 g of the title compound (yield: 85%) as an oily product.

Workup

  1. temperatureAfter cooled to room temperature
  2. washThe organic layer was washed with 1N hydrochloric acid and saturated saline
  3. customdried
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 40:1 to 9:1)

Sources & evidence

ORD record
ord-c9ad6ef77ab9431db93cf73279c8fc9c
Source dataset
uspto-grants-2012_10
Patent number
US08288390B2

Reaction notes

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