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

HRID 1850369Notes

Reaction equation

HRID 1850369 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-09d8c9e238464eb8840ccef0249de3c8
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

Loading…