Water → HCID 54156548, compound

HRID 436188Notes

Reaction equation

HRID 436188 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=2)[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[C:23]([CH3:26])([CH3:25])[CH3:24].[C:27]1(C)[CH:32]=CC(S(O)(=O)=O)=[CH:29][CH:28]=1.O>C(O)CCC.C1(C)C=CC=CC=1>[CH2:32]([O:10][C:9](=[O:11])[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C:19]([CH3:20])([CH3:22])[CH3:21])[CH:13]=1)[C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:4]=1)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 9841649HCID 9841649, compound

Product 1

HCID 54156548HCID 54156548, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 1140TolueneSolvent

Procedure

35.6 g of bis(4-hydroxy-3-tert.-butyl-phenyl)ethanoic acid (0.1 mol) were dissolved in a mixture of 222 g of n-butanol and 240 g of toluene. As an esterification catalyst, 1 g of p-toluene-sulfonic acid was added. Azeotropic distillation was continued until 1.8 mol of water had separated at the separator. The butanol-toluene phase was washed with 10% sodium bicarbonate solution and then with water. The solvent mixture was distilled off and the residue was dissolved and precipitated in 300 ml of heptane. After distillation of the solvent, 38 g (92 %, calculated on the acid used) of bis(4'-hydroxy-3'-tert-butyl-phenyl)ethanoic acid n-butyl ester were obtained, m.p. 124° C.

Workup

  1. distillationAzeotropic distillation
  2. customhad separated at the separator
  3. washThe butanol-toluene phase was washed with 10% sodium bicarbonate solution
  4. distillationThe solvent mixture was distilled off
  5. dissolutionthe residue was dissolved
  6. customprecipitated in 300 ml of heptane
  7. distillationAfter distillation of the solvent, 38 g (92 %
  8. customwere obtained

Sources & evidence

ORD record
ord-63e95230103c41c58bb601b4ae5ce827
Source dataset
uspto-grants-1977_02
Patent number
US04007282

Reaction notes

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