p-Toluenesulfonic acid → HCID 86734482, compound

HRID 436190Notes

Reaction equation

HRID 436190 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:16]=2)([CH3:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[C:26]([CH3:29])([CH3:28])[CH3:27].[C:30]1(C)[CH:35]=CC(S(O)(=O)=O)=[CH:32][CH:31]=1>C1(C)C=CC=CC=1>[CH2:35]([O:12][C:11](=[O:13])[CH2:10][CH2:9][C:8]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:16]=1)([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:4]=1)[CH3:14])[CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20556674HCID 20556674, compound

Product 1

HCID 86734482HCID 86734482, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

39.8 g of 4,4-bis(4'-hydroxy-3'-tert.-butyl-phenyl) pentanoic acid were dissolved in 222 g of n-bitanol and 228 g of toluene and 1 g of p-toluene-sulfonic acid was added as an esterification catalyst. Azeotropic distillation was continued until no more water distilled over. After toluene and butanol had been distilled off, a resin-like residue was obtained. After recrystallization from hexane, the 4,4-bis(4'-hydroxy-3'-tert.-butyl-phenyl)pentanoic acid n-butyl ester was obtained as a white crystallized substance.

Workup

  1. additionwas added as an esterification catalyst
  2. distillationAzeotropic distillation
  3. distillationdistilled over
  4. distillationAfter toluene and butanol had been distilled off
  5. customa resin-like residue was obtained
  6. customAfter recrystallization from hexane

Sources & evidence

ORD record
ord-a0d77d90e75f4683b32379d5286e1c57
Source dataset
uspto-grants-1977_02
Patent number
US04007282

Reaction notes

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