4-Hydroxybenzoic Acid → 4-(Hexanoyloxy)benzoic acid

HRID 1632914Notes

Reaction equation

HRID 1632914 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11](Cl)(=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl>N1C=CC=CC=1>[C:11]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 67340Hexanoyl chloride

Product 1

HCID 200636454-(Hexanoyloxy)benzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

10 g 4-hydroxybenzoic acid was dissolved in 50 ml dry pyridine. The solution was then externally cooled with ice water while 10.5 g hexanoyl chloride was added dropwise. After the resultant mixture had been further stirred overnight at room temperature, it was poured in 300 ml 3-N dilute hydrochloric acid. White precipitate was taken up by filtration. By recrystallizing the white precipitate in a mixed solvent of methanol/water (3:2), 14.8 g 4-hexanoyloxybenzoic acid was obtained in 87% yield based upon the amount of the hydroxybenzoic acid.

Workup

  1. additionwas added dropwise
  2. filtrationWhite precipitate was taken up by filtration
  3. customBy recrystallizing the white precipitate in a mixed solvent of methanol/water (3:2)

Sources & evidence

ORD record
ord-d74971214c324f52b734ccd49b6568af
Source dataset
uspto-grants-1984_10
Patent number
US04478741

Reaction notes

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