p-Toluenesulfonic acid monohydrate → HCID 3080102, compound

HRID 329593Notes

Reaction equation

HRID 329593 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16](O)[CH:17]2[CH2:21][O:20][N:19]([CH3:22])[C:18]2=[O:23])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])[CH:16]=[C:17]1[CH2:21][O:20][N:19]([CH3:22])[C:18]1=[O:23])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 14773917HCID 14773917, compound

Product 1

HCID 3080102HCID 3080102, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 20 g (60 mmol) of 4-[(3,5-di-tert-butyl-4-hydroxyphenyl)hydroxymethyl]-2-methyl-3-isoxazolidinone and 0.4 g of p-toluenesulfonic acid monohydrate in 300 ml of benzene was refluxed for 5 hours. The reaction mixture was concentrated and the concentrate triturated in 150 ml of ether to yield 10 g of the E-isomer of 4-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-methyl-3-isoxazolidinone having a melting point of 194°-196° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe concentrate triturated in 150 ml of ether

Sources & evidence

ORD record
ord-4fec30971ec9430692a744e9b32a12ef
Source dataset
uspto-grants-1990_01
Patent number
US04892870

Reaction notes

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