Hydrochloric Acid → HCID 14773917, compound

HRID 329592Notes

Reaction equation

HRID 329592 reaction equation
Br[CH:2]1[CH2:6][O:5][N:4]([CH3:7])[C:3]1=[O:8].[C:9]([C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[CH:16]=[O:17])([CH3:12])([CH3:11])[CH3:10].C(Cl)Cl.Cl>C1C=CC=CC=1.[Zn]>[C:22]([C:19]1[CH:18]=[C:15]([CH:16]([OH:17])[CH:2]2[CH2:6][O:5][N:4]([CH3:7])[C:3]2=[O:8])[CH:14]=[C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:20]=1[OH:21])([CH3:25])([CH3:23])[CH3:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 14773916HCID 14773916, compound

Product 1

HCID 14773917HCID 14773917, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 241BenzeneSolvent

Procedure

A mixture of 6 g (33.3 mmol) of 4-bromo-2-methyl-3-isoxazolidinone, 7 g (30 mmol) of 3,5-di-tert-butyl-4-hydroxybenzaldehyde and 3.25 g (50 mmol) of zinc dust in 125 ml of benzene was refluxed with stirring. One hour later another 3 g of zinc dust was added and, after refluxing for an additional 17 hours, the reaction mixture was stirred for five minutes with 200 ml of methylene chloride and 150 ml of 0.5N hydrochloric acid. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated to yield 10 g of crude material. This material was chromatographed on silica gel with 80% ethyl acetatehexane and recrystallized from ether-hexane to afford 5.7 g (17.1 mmol, 57%) of 4-[(3,5-di-tert-butyl-4-hydroxyphenyl)hydroxymethyl]-2-methyl-3-isoxazolidinone, mp 137°-140° C.

Workup

  1. temperaturewas refluxed
  2. temperatureafter refluxing for an additional 17 hours
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto yield 10 g of crude material
  7. customThis material was chromatographed on silica gel with 80% ethyl acetatehexane
  8. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-bdff0081a6e84e4ab2a7fea0fb6ea699
Source dataset
uspto-grants-1990_01
Patent number
US04892870

Reaction notes

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