p-Toluenesulfonic acid monohydrate → dihydro-4-(3,5-di tert-butyl-4-hydroxybenzylidene)-2-isopropyl-2H-1,2-oxazin-3(4H)-one

HRID 329598Notes

Reaction equation

HRID 329598 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16](O)[CH:17]2[CH2:22][CH2:21][O:20][N:19]([CH:23]([CH3:25])[CH3:24])[C:18]2=[O:26])[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]([CH3:14])([CH3:13])[CH3:15])[C:10]=1[OH:11])[CH:16]=[C:17]1[CH2:22][CH2:21][O:20][N:19]([CH:23]([CH3:24])[CH3:25])[C:18]1=[O:26])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19871095dihydro-4-[(3,5-di-tert-butyl-4-hydroxyphenyl)hydroxymethyl]-2-isopropyl-2H-1,2-oxazin-3(4H)-one

Product 1

HCID 54482591dihydro-4-(3,5-di tert-butyl-4-hydroxybenzylidene)-2-isopropyl-2H-1,2-oxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The dihydro-4-[(3,5-di-tert-butyl-4-hydroxyphenyl)hydroxymethyl]-2-isopropyl-2H-1,2-oxazin-3(4H)-one of Step B was refluxed in 40 ml of benzene with a catalytic amount of p-toluenesulfonic acid monohydrate for 6 hours and concentrated in vacuo. The concentrate was triturated in ether and filtered to yield 0.9 g (2.5 mmol) of dihydro-4-(3,5-di tert-butyl-4-hydroxybenzylidene)-2-isopropyl-2H-1,2-oxazin-3(4H)-one, mp 181°-183° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe concentrate was triturated in ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ff4ba197465648b1b9e33075990df3d2
Source dataset
uspto-grants-1990_01
Patent number
US04892870

Reaction notes

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