1,4-Butanediol → 4-(3-Tert-butyl-5-methyl-4-hydroxyphenyl)butanol

HRID 1721413Notes

Reaction equation

HRID 1721413 reaction equation
[OH-].[K+].[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[OH:14])([CH3:6])([CH3:5])[CH3:4].[CH2:15](O)[CH2:16][CH2:17][CH2:18][OH:19]>>[C:3]([C:7]1[CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:10]=[C:9]([CH3:13])[C:8]=1[OH:14])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 3

HCID 80641,4-ButanediolHCID 14797Potassium HydroxideHCID 166782-tert-Butyl-6-methylphenol

Product 1

HCID 211993444-(3-Tert-butyl-5-methyl-4-hydroxyphenyl)butanol

Conditions

Temperature
235 °C

Procedure

50 g of potassium hydroxide, 316 g of 2-tert-butyl-6-methylphenol and 866 g of 1,4-butanediol are initially introduced into an autoclave. After introducing nitrogen gas, the autoclave is closed and the mixture is heated at 235° C. (4 bar) for 6 hours, with stirring; a further rise in pressure as a consequence of the reaction is prevented by blowing of gas. When the reaction is complete, the reaction mixture is cooled to 80° C. and the autoclave is emptied. Excess butanediol is removed by distillation. The distillation residue is poured into 11 of water and 500 ml of toluene. The organic phase is then washed with water until neutral and the toluene is stripped off by applying a vacuum. The remaining residue (310 g) contains 68-70% of the title product of the formula ##STR25##

Workup

  1. additionAfter introducing nitrogen gas
  2. customthe autoclave is closed
  3. temperaturethe reaction mixture is cooled to 80° C.
  4. customExcess butanediol is removed by distillation
  5. additionThe distillation residue is poured into 11 of water and 500 ml of toluene
  6. washThe organic phase is then washed with water until neutral and the toluene

Sources & evidence

ORD record
ord-0c75f0beb66a47fda5b373700f6c334a
Source dataset
uspto-grants-1996_04
Patent number
US05510402

Reaction notes

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