Propylene Oxide → 3,5-Bis(1,1-dimethylethyl)-4-hydroxy-β-methylbenzeneethanol

HRID 746236Notes

Reaction equation

HRID 746236 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:10]=1[OH:19])([CH3:8])([CH3:7])[CH3:6].[CH2:20]1[O:23][CH:21]1[CH3:22]>C1(C)C=CC=CC=1>[C:15]([C:11]1[CH:12]=[C:13]([CH:21]([CH3:22])[CH2:20][OH:23])[CH:14]=[C:9]([C:5]([CH3:8])([CH3:7])[CH3:6])[C:10]=1[OH:19])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 314052,6-Di-tert-butylphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 137098813,5-Bis(1,1-dimethylethyl)-4-hydroxy-β-methylbenzeneethanolYield 16%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a stirred slurry of 66.7 g (0.5 mole) aluminum chloride in 250 ml toluene, 103.0 g (0.5 mole) 2,6-di-tert-butylphenol dissolved in 250 ml toluene was slowly added through a dropping funnel under a nitrogen atmosphere and under dry ice/acetone bath cooling so as to maintain the temperature of the mixture at -25° C. to -20° C. The addition was complete in 10 minutes. To the resulting orange-yellow slurry, 87.0 g (1.5 mole) propylene oxide dissolved in 250 ml toluene dropwise with stirring was slowly added over a period of 1.5 hours while maintaining the temperature at -35° C. to -30° C. After stirring for an additional 0.5 hours, the mixture was worked up as described in Example 1 to give 21.2 g (16% yield) of the desired product as colorless needles. This product proved identical to that obtained in Example 1 based on IR and NMR analysis.

Workup

  1. additionwas slowly added through a dropping funnel under a nitrogen atmosphere and under dry ice/acetone bath
  2. temperaturecooling so as
  3. temperatureto maintain the temperature of the mixture at -25° C. to -20° C
  4. additionThe addition
  5. additionwas slowly added over a period of 1.5 hours
  6. temperaturewhile maintaining the temperature at -35° C. to -30° C
  7. stirringAfter stirring for an additional 0.5 hours

Sources & evidence

ORD record
ord-636083c93b834a93878f507f79b5a231
Source dataset
uspto-grants-1986_07
Patent number
US04603161

Reaction notes

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