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

HRID 972087Notes

Reaction equation

HRID 972087 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:21])=O>N1C=CC=CC=1.C1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([Cl:21])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

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 2

HCID 1049PyridineCatalystHCID 241BenzeneSolvent

Conditions

Temperature
45 °C

Procedure

To a 3-necked flask equipped with a magnetic stirrer, thermometer, and water condenser with a drying tube is added 3,5-di-t-butyl-4-hydroxybenzoic acid (12.5 g, 0.05 m), thionyl chloride (10 ml) and 5 drops of pyridine. This mixture is heated at 45° C. for 1.5 hr. After cooling to RT, 50 ml of benzene is added. After stirring for 15 min., the benzene is evaporated under water aspirator vacuum leaving a yellow solid. This is dissolved in petroleum ether (at 35°-55° C.), filtered, and evaporated to afford 11 g of a yellow solid, mp 90°-93° (lit.mp. 96°-99°).

Workup

  1. customTo a 3-necked flask equipped with a magnetic stirrer
  2. temperatureAfter cooling to RT
  3. customthe benzene is evaporated under water
  4. customleaving a yellow solid
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6c32e8d6c71742d6bb7b8a4a8d83db73
Source dataset
uspto-grants-1979_07
Patent number
US04163008

Reaction notes

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