tert-Butanol → 3,5-Di-tert-butyl-4-hydroxybenzaldehyde

HRID 1973055Notes

Reaction equation

HRID 1973055 reaction equation
[C:1]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=[C:7]([CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].BrBr.C([OH:23])(C)(C)C>>[C:12]([C:9]1[CH:8]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[OH:11])[CH:16]=[O:23])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 24408BromineHCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Procedure

In a 5 l., four-neck, round-bottom flask equipped with a thermometer, mechanical stirrer, dropping funnel and vent tube were placed 600 gm. of 2.6-di-t-butyl-p-cresol and 3600 ml. of t-butyl alcohol. To this stirred solution at 25°-35° C were added 908 gm. of Br2 over a period of ten hours. The resulting solid was separated by filtration, washed with hexane and dried. The yield was 440 gm. (71%) of aldehyde melting at 187°-189° C.

Workup

  1. custom, four-neck, round-bottom flask equipped with a thermometer, mechanical stirrer
  2. additionTo this stirred solution at 25°-35° C were added 908 gm
  3. customThe resulting solid was separated by filtration
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-aeb6897b04904f8e8048c4bec82c7358
Source dataset
uspto-grants-1976_12
Patent number
US03996194

Reaction notes

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