Phthalic Acid → 3-Butylphthalic acid

HRID 1710302Notes

Reaction equation

HRID 1710302 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([OH:6])=[O:5].[OH-].[K+]>C(O)CCC>[CH2:1]([C:10]1[CH:9]=[CH:8][CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]=1[C:1]([OH:12])=[O:11])[CH2:2][CH2:10][CH3:9]

Participants

4

Reactant 2

HCID 1017Phthalic AcidHCID 14797Potassium Hydroxide

Product 1

HCID 139815183-Butylphthalic acid

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

148.2 g of anhydrous phthalic acid and 1.05 times the molar equivalent 77.8 g of n-butyl alcohol were added to a 500 ml glass round-bottomed flask equipped with stirring blades, thermometer and Dimroth condenser, heated while slowly stirring, and after the generated heat at about 90° C. wore off, raised to a temperature of 130° C., which was maintained for 2 hours. The mixture was subsequently cooled to 60° C. The acid value (number of mg of KOH necessary to neutralize 1 g of a sample) of the reaction solution was 253.8. Since the acid value for the case where the reaction is 100% complete is 248.4, the reaction rate was computed to be 98%.

Workup

  1. customequipped with stirring blades
  2. temperaturethermometer and Dimroth condenser, heated
  3. temperatureraised to a temperature of 130° C., which
  4. temperaturewas maintained for 2 hours
  5. temperatureThe mixture was subsequently cooled to 60° C

Sources & evidence

ORD record
ord-37a2dd553a0740b287bc876f24adabae
Source dataset
uspto-grants-2010_09
Patent number
US07790290B2

Reaction notes

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