Ethanol → 75546-54-2

HRID 2084747Notes

Reaction equation

HRID 2084747 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+].C(O)C.[CH2:21]([OH:24])[CH:22]=[CH2:23].C1(C)C=CC=CC=1>[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4]>[C:8]([C:4]1[CH:5]=[C:6]([CH2:23][CH2:22][CH2:21][OH:24])[CH:7]=[C:2]([CH3:1])[C:3]=1[OH:12])([CH3:9])([CH3:11])[CH3:10]

Participants

8

Reactant 6

HCID 702EthanolHCID 887Methanol2×HCID 1140TolueneHCID 7858Allyl AlcoholHCID 166782-tert-Butyl-6-methylphenolHCID 10942334Sodium Methoxide

Product 1

HCID 685085675546-54-2Yield 78%

Reagents, catalysts & solvents 1

HCID 76524Titanium tetraethoxideCatalyst

Conditions

Temperature
210 °C

Procedure

A pressure container was charged with 62.4 g (0.38 mol) of 2-methyl-6-t-butylphenol, 14.7 g (0.076 mol) of a methanol solution containing 28% sodium methoxide and 17.4 g (0.076 mol) of titanium tetraethoxide. The mixture was heated under reduced pressure to distill a mixture of 13.0 g (0.41 mol) of methanol and 14.1 g (0.31 mol) of ethanol out of the reaction system. Thereafter, 53.2 g (0.92 mol) of allyl alcohol and 38.7 g (0.42 mol) of toluene were added to the reaction system and the atmosphere in the reaction system was replaced by nitrogen. Then, the reaction system was tightly closed, heated up to 210° C. and kept at that temperature for 7 hours. Then, the reaction system was cooled to room temperature. A sample of the reaction solution was analyzed by gas-chromatography. The desied product, 3-(3-t-butyl-4-hydroxy-5-methylphenyl)propanol was obtained in a yield of 78%.

Workup

  1. temperatureThe mixture was heated under reduced pressure
  2. distillationto distill
  3. customThen, the reaction system was tightly closed
  4. temperatureThen, the reaction system was cooled to room temperature

Sources & evidence

ORD record
ord-64b0e4ad9c5b4480b6f2965343f3addb
Source dataset
uspto-grants-2004_04
Patent number
US06717020B2

Reaction notes

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