Water → p-(1-Methyl-heptyloxy)benzoic acid

HRID 568755

Reaction equation

HRID 568755 reaction equation
[OH-:1].[K+].[CH3:3][CH:4]([O:11]S(C1C=CC(C)=CC=1)(=O)=O)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH2:22].[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[CH3:3][CH:4]([O:11][C:26]1[CH:27]=[CH:28][C:23]([C:29]([OH:22])=[O:1])=[CH:24][CH:25]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 14797Potassium HydroxideHCID 3912199p-Toluenesulfonic acid 1-methylheptyl ester

Product 1

HCID 13878419p-(1-Methyl-heptyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl p-hydroxybenzoate ester (177.0 g, 1.16 mol) was dissolved in methanol (800 ml), followed by adding KOH (65.0 g, 1.16 mol), adding after completion of heat generation, optically active p-toluenesulfonic acid 1-methyl-heptyl ester (300.0 g, 1.06 mol) prepared in advance, refluxing the mixture for about 4 hours, allowing it to stand at room temperature, thereafter adding water (1 l) and toluene (500 ml), agitating the mixture, washing the separated toluene layer sufficiently with 2N-NaOH aqueous solution and further with water until the wash water became neutral, distilling off toluene, dissolving the residue in ethanol (50 ml), adding a solution of NaOH (30.0 g) dissolved in water (150 ml), refluxing the mixture for about one hour, thereafter acidifying the reaction product with hydrochloric acid, filtering deposited crystals and recrystallizing from heptane to obtain optically active p-(1-methyl-heptyloxy)benzoic acid (96.2 g).

Workup

  1. customprepared in advance
  2. temperaturerefluxing the mixture for about 4 hours
  3. customto stand at room temperature
  4. washwashing the separated toluene layer sufficiently with 2N-NaOH aqueous solution
  5. distillationdistilling off toluene
  6. dissolutiondissolving the residue in ethanol (50 ml)
  7. additionadding a solution of NaOH (30.0 g)
  8. dissolutiondissolved in water (150 ml)
  9. temperaturerefluxing the mixture for about one hour
  10. filtrationfiltering
  11. customrecrystallizing from heptane

Sources & evidence

ORD record
ord-828201eec95f4b19bb5a86e6babf9552
Source dataset
uspto-grants-1988_03
Patent number
US04729847

Linked notes

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