p-Toluenesulfonic acid monohydrate → HCID 53886128, compound

HRID 329599Notes

Reaction equation

HRID 329599 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]([CH2:23][CH3:24])[C:18]2=[O:25])[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]([CH3:13])([CH3:15])[CH3:14])[C:10]=1[OH:11])[CH:16]=[C:17]1[CH2:22][CH2:21][O:20][N:19]([CH2:23][CH3:24])[C:18]1=[O:25])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19871113HCID 19871113, compound

Product 1

HCID 53886128HCID 53886128, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The dihydro-4-[(3,5-di-tert-butyl-4-hydroxyphenyl)hydroxymethyl]-2-ethyl-2H-1,2-oxazin-3(4H)-one (15 g, 41 mmol) obtained according to Step B was added to 100 ml of benzene and 0.4 g of p-toluenesulfonic acid monohydrate and refluxed for 13 hours. The mixture was concentrated to a solid, taken up in 150 ml of methylene chloride, washed with dilute sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated to a brown solid (14.1 g) which was recrystallized from acetone to yield 6.4 g of crystalline dihydro-4-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-ethyl-2H-1,2-oxazin-3(4H)-one having a melting point of 166°-167° C.

Workup

  1. temperaturerefluxed for 13 hours
  2. concentrationThe mixture was concentrated to a solid
  3. washwashed with dilute sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to a brown solid (14.1 g) which
  6. customwas recrystallized from acetone

Sources & evidence

ORD record
ord-6a43bd772c7a4736b18373d9d8a9cc6a
Source dataset
uspto-grants-1990_01
Patent number
US04892870

Reaction notes

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