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

HRID 1017153Notes

Reaction equation

HRID 1017153 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].S(Cl)([Cl:20])=O>>[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%

Procedure

3,5-Di-t-butylbenzoic acid, purchased from Aldrich Chemical Co., (10 g, 0.042 mol) was dissolved in 50 mL thionyl chloride and the light yellow solution was refluxed for 3 h under argon. The reaction was cooled to room temperature and excess SOCl2 was evaporated under vacuum (liq. N2 trap). The resulting oil was dissolved in dry toluene (100 mL) and the resulting solution was evaporated under vacuum to give the 3,5-di-t-butylbenzoyl chloride as a light brown oil (10.5 g, 99%).

Workup

  1. temperaturethe light yellow solution was refluxed for 3 h under argon
  2. customexcess SOCl2 was evaporated under vacuum (liq. 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-a581f50829014820a169fc79e2830023
Source dataset
uspto-grants-2002_11
Patent number
US06479424B1

Reaction notes

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