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

HRID 1606412Notes

Reaction equation

HRID 1606412 reaction equation
[OH-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:14]=1[OH:15])[CH:10]=[O:11])([CH3:6])([CH3:5])[CH3:4].[CH3:20][C:21]([CH3:23])=[O:22].Cl>C(O)C.O>[CH3:20][C:21]([CH:23]=[CH:10][C:9]1[CH:8]=[C:7]([C:3]([CH3:4])([CH3:6])[CH3:5])[C:14]([OH:15])=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:12]=1)=[O:22].[C:16]([C:13]1[CH:12]=[C:9]([CH:8]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:14]=1[OH:15])[CH:10]=[O:11])([CH3:19])([CH3:18])[CH3:17]

Participants

8

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 2

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeYield 94%HCID 215849HCID 215849, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3,5-di tert.butyl-4-hydroxystyryl methyl ketone was prepared by adding a solution of 8 grams of sodium hydroxide in 100 milliliters of absolute ethanol to a mixture of 23.4 grams of 3,5-di tert.butyl-4-hydroxybenzaldehyde and 58 grams of acetone. The reaction mixture was stirred at room temperature for 14 hours and then at reflux temperature for 71/2 hours. After cooling, it was poured into 500 milliliters of water and the resulting mixture was neutralized by the addition of dilute hydrochloric acid. The sticky solid which precipitated was filtered off and mixed with petroleum ether. Filtration yielded 11 grams of unreacted 3,5-di tert.butyl-4-hydroxybenzaldehyde. From the filtrate was isolated 5.5 grams of the desired product which melted at 101° to 105° C.

Workup

  1. temperatureat reflux temperature for 71/2 hours
  2. temperatureAfter cooling
  3. customThe sticky solid which precipitated
  4. filtrationwas filtered off
  5. additionmixed with petroleum ether
  6. filtrationFiltration

Sources & evidence

ORD record
ord-dcc0dc544a45492ea6d918666d20bfac
Source dataset
uspto-grants-1976_04
Patent number
US03953398

Reaction notes

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