Water → 4-Propoxybenzoic Acid

HRID 493026노트

반응식

HRID 493026 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 7456MethylparabenHCID 78401-BromopropaneHCID 14797Potassium Hydroxide

생성물 1

HCID 1385004-Propoxybenzoic Acid수율 96%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e6c285b9cbff41db9742919c3f3e984c
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534547B2

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