4-Hydroxybenzoic Acid → (R)-4-(2-n-Hexyloxypropanoyloxy)benzoic acid

HRID 653586Notes

Reaction equation

HRID 653586 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH2:11]([O:17][C@H:18]([CH3:22])[C:19](Cl)=[O:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C(Cl)Cl.N1C=CC=CC=1.Cl>[CH2:11]([O:17][C@H:18]([CH3:22])[C:19]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 22844813(R)-2-n-hexyloxypropanoyl chloride

Product 1

HCID 53844545(R)-4-(2-n-Hexyloxypropanoyloxy)benzoic acidYield 46.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of p-hydroxybenzoic acid (2.15 g, 15.6 mmol) in methylene chloride (30 ml) and pyridine (10 ml), a solution of (R)-2-n-hexyloxypropanoyl chloride (3.0 g, 15.6 mmol) in methylene chloride (20 ml) was added dropwise and then the mixture was refluxed for 7 hours. After cooling, the resultant mixture was taken up in dilute hydrochloric acid, extracted with ethyl ether; the organic extract was washed twice with dilute hydrochloric acid and with H2O for four times, and dried over anhydrous Na2SO4. The solvent was evaporated and the residue was recrystallized from n-hexane to afford 2.13 g of the title compound as white crystals; mp. 67.0°-72.0° C.

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl ether
  4. extractionthe organic extract
  5. washwas washed twice with dilute hydrochloric acid and with H2O for four times
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was evaporated
  8. customthe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-cebb72eb614344888255493de3f11674
Source dataset
uspto-grants-1992_07
Patent number
US05128062

Reaction notes

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