3,5-Di-tert-butyl-4-hydroxybenzaldehyde → dihydro-4-[(3,5-di-tert-butyl-4-hydroxyphenyl)hydroxymethyl]-2-isopropyl-2H-1,2-oxazin-3(4H)-one

HRID 329597Notes

Reaction equation

HRID 329597 reaction equation
Br[CH:2]1[CH2:7][CH2:6][O:5][N:4]([CH:8]([CH3:10])[CH3:9])[C:3]1=[O:11].[C:12]([C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[CH:19]=[O:20])([CH3:15])([CH3:14])[CH3:13]>C1C=CC=CC=1.[Zn]>[C:25]([C:22]1[CH:21]=[C:18]([CH:19]([OH:20])[CH:2]2[CH2:7][CH2:6][O:5][N:4]([CH:8]([CH3:10])[CH3:9])[C:3]2=[O:11])[CH:17]=[C:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:23]=1[OH:24])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 19871116Dihydro-4-Bromo-2-Isopropyl-2H-1,2-Oxazin-3(4H)-One

Product 1

HCID 19871095dihydro-4-[(3,5-di-tert-butyl-4-hydroxyphenyl)hydroxymethyl]-2-isopropyl-2H-1,2-oxazin-3(4H)-oneYield 63.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

A stirred mixture of 1.1 g (5 mmol) dihydro-4-bromo-2-isopropyl-2H-1,2-oxazin-3(4H)-one, 1.2 g (5 mmol) of 3,5-di-tert-butyl-4-hydroxybenzaldehyde and 1 g of zinc dust in 20 ml of benzene were refluxed for 15 hours and concentrated. The concentrate was taken up in methylene chloride and chromatographed on silica gel with 30% ethyl acetate-hexane to yield 1.2 g of dihydro-4-[(3,5-di-tert-butyl-4-hydroxyphenyl)hydroxymethyl]-2-isopropyl-2H-1,2-oxazin-3(4H)-one, mp 150°-153° C.

Workup

  1. temperaturewere refluxed for 15 hours
  2. concentrationconcentrated
  3. customchromatographed on silica gel with 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-f362ba63fe9f424486d9734c5733c634
Source dataset
uspto-grants-1990_01
Patent number
US04892870

Reaction notes

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