Hydrochloric Acid → 4-[2-(4-Hydroxyphenyl)propan-2-yl]-2-methylphenol

HRID 1659606Notes

Reaction equation

HRID 1659606 reaction equation
Cl.[C:2](C1C=CC(O)=CC=1)(C)=C.[CH3:12][C:13]([C:22]1[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=1)([C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)[CH3:14].[OH-].[Na+].C1(C)C(O)=CC=CC=1>>[CH3:2][C:17]1[CH:16]=[C:15]([C:13]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)([CH3:12])[CH3:14])[CH:20]=[CH:19][C:18]=1[OH:21]

Participants

6

Reactant 5

HCID 313Hydrochloric Acid2×HCID 335O-Cresol2×HCID 6623Bisphenol AHCID 14798Sodium HydroxideHCID 584247p-Isopropenylphenol

Product 1

HCID 143890094-[2-(4-Hydroxyphenyl)propan-2-yl]-2-methylphenol

Procedure

Anhydrous HCl was introduced, with adequate cooling, into a mixture of 134 g (1.0 mole) of freshly prepared 4-isopropenylphenol (made by thermally cracking BPA in the presence of catalytic amounts of sodium hydroxide and separating it from the coproduct phenol by fractional vacuum distillation) and 540 g (5.0 moles) of o-cresol, while maintaining the temperature of the ensuing exothermic reaction below 50° C. After 4 hours, the red colored reaction mixture was stripped of HCl and excess cresol under water aspirator vacuum and the resultant straw colored melt was purified by recrystallization from cyclohexane. The 98.7% pure MMEP had a mp of 112°-113° C.

Workup

  1. customseparating it from the coproduct phenol
  2. temperaturewhile maintaining
  3. customthe temperature of the ensuing exothermic reaction below 50° C
  4. customthe resultant straw colored melt was purified by recrystallization from cyclohexane

Sources & evidence

ORD record
ord-105a538dde964662be042e60af7ad9db
Source dataset
uspto-grants-1981_12
Patent number
US04304899

Reaction notes

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