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

HRID 1492892Notes

Reaction equation

HRID 1492892 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.CS(C)=O.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].Cl>[OH-].[Na+]>[CH2:16]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 81401-Bromooctane

Product 1

HCID 172314-(Octyloxy)benzoic acidYield 39.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-hydroxybenzoic acid (19.2 g) in 10% NaOH (120 ml) was dropwise added to 480 ml of dimethyl sulfoxide over 30 minutes during which the temperature in reaction mixture was controlled between 30° and 40° C. After adding, the solution was cooled to 17°-20° C. 1-Bromooctane (28.95 g) was dropwise added to the solution over 30 minutes and the reaction mixture was vigorously stirred for 4 hours at room temperature. The reaction mixture was poured into ice water (1200 ml) and acidified with 40 ml of conc. hydrochloric acid. After vigorously stirring for another 1 hour, the resulting solid was removed by filtration and dissolved in 60 ml of acetonitrile. The solution was refluxed over 30 minutes and was allowed to stand overnight at room temperature to yield 4-octyloxybenzoic acid (13.8 g) as a crystal (MP 96° C., Anal Calcd. for C15H22O 3 : C 71.97, H 8.86, Found: C 71.30, H 8.89).

Workup

  1. customin reaction mixture
  2. customwas controlled between 30° and 40° C
  3. additionAfter adding
  4. temperaturethe solution was cooled to 17°-20° C
  5. stirringAfter vigorously stirring for another 1 hour
  6. customthe resulting solid was removed by filtration
  7. dissolutiondissolved in 60 ml of acetonitrile
  8. temperatureThe solution was refluxed over 30 minutes
  9. waitto stand overnight at room temperature

Sources & evidence

ORD record
ord-489a7b61adc24ee08c47b895d666ae9d
Source dataset
uspto-grants-1994_12
Patent number
US05376634

Reaction notes

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