Potassium Hydroxide → 2,6-Dipropoxybenzoic acid

HRID 1534055Notes

Reaction equation

HRID 1534055 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][CH2:17][CH3:18])[C:6]=1[C:7]([O:9]C)=[O:8])[CH2:2][CH3:3].[OH-].[K+]>C(O)C>[CH2:16]([O:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[C:6]=1[C:7]([OH:9])=[O:8])[CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19911958Methyl 2,6-dipropoxybenzoate

Product 1

HCID 132342692,6-Dipropoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2,6-dihydroxybenzoate was reacted with n-propyl iodide in the presence of sodium hydride to provide methyl 2,6-di-n-propoxybenzoate. The ester thus formed was saponified by reaction with 40% aqueous potassium hydroxide in ethanol to afford 2,6-di-n-propoxybenzoic acid. A 20 g portion of the acid was then reacted with 30 g of thionyl chloride in 100 ml of benzene at reflux for five hours. Removal of the solvent by evaporation under reduced pressure and purification of the product by distillation provided 4.88 g of 2,6-di-n-propoxybenzoyl chloride. B.P. 135°-140° C. at 0.2 torr.

Sources & evidence

ORD record
ord-97a948d8ba2b448383b471c0e4da2503
Source dataset
uspto-grants-1992_02
Patent number
US05086184

Reaction notes

Loading…