4-tert-Butylphthalic acid → 4-tert-Butylphthalic anhydride

HRID 2073402Notes

Reaction equation

HRID 2073402 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:14]([OH:16])=[O:15])[C:8](=[CH:12][CH:13]=1)[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2]>S(Cl)(Cl)=O>[C:1]([C:5]1[CH:6]=[C:7]2[C:14](=[O:15])[O:16][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 6051744-tert-Butylphthalic acid

Product 1

HCID 1229304-tert-Butylphthalic anhydrideYield 94.2%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Subsequently, a 1 liter round bottom flask was fitted with a reflux condenser, to which was added 173.66 grams (0.7814 mole) of 4-t-butylphthalic acid and 500 milliliters of thionyl chloride. The yellow solution was magnetically stirred and refluxed for 3 hours, after which the thionyl chloride was removed from the anhydride under reduced pressure. The resultant white crystalline solid was washed three times with anhydrous hexane and the hexane was removed under reduced pressure to yield 150.33 grams (0.7361 mole) of the 4-t-butyl-phthalic anhydride product, which exhibited a melting point of 77° to 78° C. The identity of the 4-t-butyl-phthalic anhydride product was confirmed by IR spectrum.

Workup

  1. customSubsequently, a 1 liter round bottom flask was fitted with a reflux condenser, to which
  2. temperaturerefluxed for 3 hours
  3. customafter which the thionyl chloride was removed from the anhydride under reduced pressure
  4. washThe resultant white crystalline solid was washed three times with anhydrous hexane
  5. customthe hexane was removed under reduced pressure

Sources & evidence

ORD record
ord-5ff9ad0ba5854e1e8446659ef7b89933
Source dataset
uspto-grants-1990_04
Patent number
US04916470

Reaction notes

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