1-Propanethiol, sodium salt (1:1) → 4-Hydroxy-3-(3-methoxypropoxy)benzaldehyde

HRID 1690606노트

반응식

HRID 1690606 반응식
C[O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16].C([S-])CC.[Na+]>CN(C=O)C>[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16]

참가 물질

4

반응물 2

HCID 46817251-Propanethiol, sodium salt (1:1)HCID 112183584-Methoxy-3-(3-methoxypropoxy)benzaldehyde

생성물 1

HCID 866332964-Hydroxy-3-(3-methoxypropoxy)benzaldehyde수율 97.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (22 g, 98 mmol) was dissolved in DMF (490 mL) and sodium propanethiolate (12.5 g, 127 mmol) was added. The mixture was brought to 100° C. and the reaction mixture was stirred for 30 minutes. After cooling to room temperature, solvents were evaporated under reduced pressure and the residue was dissolved in dichloromethane (200 mL) and saturated aqueous ammonium chloride (200 mL). Hydrochloric acid 1N was then added until acidic pH. The organic layer was separated and washed with water and brine, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to yield 20 g (quantitative yield) of the desired product as a yellow oil, used in the next step without further purification.

후처리

  1. customwas brought to 100° C.
  2. customsolvents were evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (200 mL)
  4. additionHydrochloric acid 1N was then added until acidic pH
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-afc3c28fb6b74f3fa4669e53b25e1d99
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153647B2

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