Acetic Acid → 3,5-Di-tert-butylsalicylaldehyde

HRID 1110159Notes

Reaction equation

HRID 1110159 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)O.[C:21](O)(=[O:23])C>>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:21]=[O:23])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 73112,4-Di-tert-butylphenol

Product 1

HCID 6880233,5-Di-tert-butylsalicylaldehydeYield 40%

Procedure

A mixture of 208.4 g (1.0 mol) of 2,4-di-tert-butylphenol and 283.2 g (2.0 mol) of HMT in 500 mL of glacial acetic acid was heated at 130 C. with stirring for 2 hours. A solution of 500 mL of 20% (vol/vol) aqueous sulfuric acid was then added and the resulting solution was refluxed for 0.5 hour. The solution was cooled to around 60°-80° C. and the organic phase was separated from the aqueous phase. The organic phase was recrystallized twice from 150-200 mL of cold (0°-5° C.) methanol to give 93 to 107 g (40-46% yield) of pure 3,5-di-tert-butylsalicylaldehyde of greater than 95% purity by HPLC. mp 60°-62° C. 1H-NMR (60 MHz, CDCl3): δ9.8 (s,1H); 7.6 (d,1H); 7.3 (d,1H); 1.2-1.5 (d,18H). IR (KBr): 3400, 2980, 1650 cm-1.

Workup

  1. temperaturewas heated at 130 C
  2. temperaturethe resulting solution was refluxed for 0.5 hour
  3. temperatureThe solution was cooled to around 60°-80° C.
  4. customthe organic phase was separated from the aqueous phase
  5. customThe organic phase was recrystallized twice from 150-200 mL of cold (0°-5° C.) methanol

Sources & evidence

ORD record
ord-002a089549694d158a5c870725dd3ffa
Source dataset
uspto-grants-1994_06
Patent number
US05324860

Reaction notes

Loading…