Methanol → 75546-54-2

HRID 2084748Notes

Reaction equation

HRID 2084748 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:3]=1[OH:12].CO.[CH2:15]([OH:18])[CH:16]=[CH2:17]>C1(C)C=CC=CC=1>[C:8]([C:4]1[CH:5]=[C:6]([CH2:17][CH2:16][CH2:15][OH:18])[CH:7]=[C:2]([CH3:1])[C:3]=1[OH:12])([CH3:9])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 7858Allyl Alcohol2×HCID 166782-tert-Butyl-6-methylphenol

Product 1

HCID 685085675546-54-2Yield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
210 °C

Procedure

To the solution obtained above after hydrogen gas evolution had ceased, 45 g (0.27 mol) of 2-methyl-6-t-butylphenol were added, and then heated under reduced pressure, thereby 15 g (0.47 mol) of methanol were removed from the reaction system. Then, 15.9 g (0.27 mol) of allyl alcohol and 13.5 g (0.15 mol) of toluene were added thereto. The resulting solution after the addition of toluene and allyl alcohol were transferred to a pressure container, and the atmosphere thereof was substituted with nitrogen gas, sealed and heated up to 210° C. and maintained at the same temperature for 4 hours. Thereafter the reaction mixture was cooled to room temperature and a sample thereof was analyzed by gas-chromatography. The desired product, 3-(3-t-butyl-4-hydroxy-5-methylphenyl)propanol was obtained in a yield of 82%.

Workup

  1. temperatureheated under reduced pressure
  2. customsealed
  3. temperaturemaintained at the same temperature for 4 hours
  4. temperatureThereafter the reaction mixture was cooled to room temperature

Sources & evidence

ORD record
ord-c929776bca274dc8ad0dcc94c8bc62a2
Source dataset
uspto-grants-2004_04
Patent number
US06717020B2

Reaction notes

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