Methanol → 75546-54-2

HRID 2084749Notes

Reaction equation

HRID 2084749 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.C[O-].[Na+].[CH2:18]([OH:21])[CH:19]=[CH2:20].C1(C)C=CC=CC=1>>[C:8]([C:4]1[CH:5]=[C:6]([CH2:20][CH2:19][CH2:18][OH:21])[CH:7]=[C:2]([CH3:1])[C:3]=1[OH:12])([CH3:9])([CH3:11])[CH3:10]

Participants

6

Reactant 5

HCID 887Methanol2×HCID 1140TolueneHCID 7858Allyl AlcoholHCID 166782-tert-Butyl-6-methylphenolHCID 10942334Sodium Methoxide

Product 1

HCID 685085675546-54-2Yield 52%

Conditions

Temperature
210 °C

Procedure

A pressure container was charged with 62.7 g (0.38 mol) of 2-methyl-6-t-butylphenol and 7.3 g (0.038 mol) of a methanol solution containing 28% of sodium methoxide. Then the mixture was heated under reduced pressure to distill 6.5 g (0.2 mol) of methanol. Thereafter, 22.2 g (0.92 mol) of allyl alcohol and 18.7 g (0.19 mol) of toluene were added to the reaction system, the atmosphere in the reaction system was replaced by nitrogen and then, the reaction system was tightly closed. Then, the reaction system was raised up to 210° C. and kept at that temperature for 7 hours. Then, the reaction mixture was cooled to room temperature. A sample of the reaction solution was analyzed by gas-chromatography. The desired product, 3-(3-t-butyl-4-hydroxy-5-methylphenyl)propanol was obtained in a yield of 52%.

Workup

  1. temperatureThen the mixture was heated under reduced pressure
  2. customthe reaction system was tightly closed
  3. temperatureThen, the reaction mixture was cooled to room temperature

Sources & evidence

ORD record
ord-fe240489dc5347d3a5f52fbadce4d954
Source dataset
uspto-grants-2004_04
Patent number
US06717020B2

Reaction notes

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