3,5-Di-tert-butyl-4-hydroxybenzoic acid → 3,5-Di-tert-butyl-4-hydroxybenzoyl chloride

HRID 2258476Notes

Reaction equation

HRID 2258476 reaction equation
[OH:1][C:2]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[C:15]([CH3:18])([CH3:17])[CH3:16].O=S(Cl)[Cl:21]>C(Cl)(Cl)Cl>[OH:1][C:2]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:5]([C:6]([Cl:21])=[O:7])=[CH:4][C:3]=1[C:15]([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4-Hydroxy-3,5-di-tert-butyl benzoic acid (12.5 g, 50 mM) was dissolved in 80 ml of chloroform. To the resulting solution was added dropwise a solution of SOCl2 (chlorination agent, 10 ml) in chloroform (20 ml), followed by heating under reflux for 3 hours. The reaction solution was then distilled off under reduced pressure to yield 4-hydroxy-3,5-di-tert-butylbenzoyl chloride.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. distillationThe reaction solution was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-e48922b45b2e4320bc5729f743d2c095
Source dataset
uspto-grants-1997_08
Patent number
US05661153

Reaction notes

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