Water → p-Propoxybenzoic acid

HRID 493026Notes

Reaction equation

HRID 493026 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].[CH3:14][CH2:15][CH2:16]Br.O>CS(C)=O>[CH2:14]([O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7456MethylparabenHCID 78401-BromopropaneHCID 14797Potassium Hydroxide

Product 1

HCID 138500p-Propoxybenzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl 4-hydroxybenzoate (15.4 g: 101.2 mmol) was dissolved in 150 ml of dimethylsulfoxide (DMSO), and an aqueous solution of potassium hydroxide (KOH/H2O: 7 g/15 ml) was added to the mixture. The resultant mixture was stirred until dissolving homogeneously. Next, 12.5 g (101.6 mmol) of n-propyl bromide was added thereto, and the reaction was carried out at a room temperature for 24 hours. The reaction mixture was poured into 1 L of an iced water and the resultant precipitate was collected by filtration. The obtained precipitate was dissolved in 300 ml of ethanol, and an aqueous solution of sodium hydroxide (NaOH/H2O: 5 g/100 ml) was added thereto. Thus obtained mixture was refluxed by heating for 1 hour, and water (the amount of the water: about 300 ml) was added thereto with removing ethanol (EtOH). After cooling to a room temperature, the transparent solution was acidified by adding a concentrated hydrochloric acid. The resultant white precipitate was filtered and recrystallized from toluene to give 17.5 g (97.2 mmol) of 4-n-propyloxybenzoic acid.

Workup

  1. dissolutionuntil dissolving homogeneously
  2. filtrationthe resultant precipitate was collected by filtration
  3. dissolutionThe obtained precipitate was dissolved in 300 ml of ethanol
  4. additionan aqueous solution of sodium hydroxide (NaOH/H2O: 5 g/100 ml) was added
  5. temperatureThus obtained mixture was refluxed
  6. temperatureby heating for 1 hour
  7. additionwater (the amount of the water: about 300 ml) was added
  8. additionby adding a concentrated hydrochloric acid
  9. filtrationThe resultant white precipitate was filtered
  10. customrecrystallized from toluene

Sources & evidence

ORD record
ord-e6c285b9cbff41db9742919c3f3e984c
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Reaction notes

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