Thionyl Chloride → 3,5-Di-t-butylbenzoyl chloride

HRID 1017158Notes

Reaction equation

HRID 1017158 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:13]=1)[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].O=S(Cl)[Cl:20]>>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:13]=1)[C:8]([Cl:20])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 853393,5-Bis(tert-butyl)benzoic acid

Product 1

HCID 118176223,5-Di-t-butylbenzoyl chlorideYield 99.3%

Procedure

3,5-Di-t-butyl benzoic acid (9.80 g, 41.81 mmol) was dissolved in SOCl2 (29.9 g, 118.9 mmol) and the light yellow solution was refluxed for three hours under argon with a NaOH trap to neutralize any acidic vapors. The reaction was cooled to room temperature and excess SOCl2 was evaporated under vacuum (liquid N2 trap). The resulting oil was dissolved in dry toluene (100 mL) and the resulting solution was evaporated under vacuum to give 3,5-di-t-butylbenzoyl chloride as a light yellow-green oil (10.5 g, 99% yield).

Workup

  1. temperaturethe light yellow solution was refluxed for three hours under argon with a NaOH trap
  2. customexcess SOCl2 was evaporated under vacuum (liquid N2 trap)
  3. dissolutionThe resulting oil was dissolved in dry toluene (100 mL)
  4. customthe resulting solution was evaporated under vacuum

Sources & evidence

ORD record
ord-b96417509df14b0caa0ecf6b99aee18d
Source dataset
uspto-grants-2002_11
Patent number
US06479424B1

Reaction notes

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