Phthalic Acid → Mono(2-phenoxyethyl)phthalic acid

HRID 1710304Notes

Reaction equation

HRID 1710304 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].[O:13]([CH2:20][CH2:21]O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[K+]>>[O:13]([CH2:20][CH2:21][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])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 1017Phthalic AcidHCID 14797Potassium HydroxideHCID 31236Phenoxyethanol

Product 1

HCID 68740870Mono(2-phenoxyethyl)phthalic acid

Conditions

Temperature
90 °C

Procedure

148.1 g of anhydrous phthalic acid and roughly the molar equivalent 139.3 g of 2-phenoxyethanol 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 1 hour. 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 212.6. Since the acid value for the case where the reaction is 100% complete is 202.2, the reaction rate was computed to be 95%.

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 1 hour
  5. temperatureThe mixture was subsequently cooled to 60° C

Sources & evidence

ORD record
ord-d73c507281524b0393b0b683101b6f99
Source dataset
uspto-grants-2010_09
Patent number
US07790290B2

Reaction notes

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