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

HRID 974706Notes

Reaction equation

HRID 974706 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 temeperature 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 drowise 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. hydochloric acid. After vigorously stirring for 1 hour, the resulting solid was removed by filtration, and dissolved in 60 ml of acetonitrile. The solution was refluxed for 30 minutes, then was allowed to stand overnight at room temperature to yield 4-octyloxybenzoic acid (13.8 g) as crystals (m.p. 96° C.; Anal: Calcd. for C15H22O3 : 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 1 hour
  6. customthe resulting solid was removed by filtration
  7. dissolutiondissolved in 60 ml of acetonitrile
  8. temperatureThe solution was refluxed for 30 minutes
  9. waitto stand overnight at room temperature

Sources & evidence

ORD record
ord-03c6fcabc22e4cd7bad2d9038528eb44
Source dataset
uspto-grants-1997_03
Patent number
USH0001638

Reaction notes

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