Sodium borohydride → 4-(3-Chloropropoxy)-3-hydroxy-alpha-methylbenzenemethanol

HRID 233852

반응식

HRID 233852 반응식
[BH4-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][C:9]=1[OH:17]>C(O)C.O1CCCC1>[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:15])[OH:16])=[CH:10][C:9]=1[OH:17]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydride2회HCID 103765071-(4-(3-Chloropropoxy)-3-hydroxyphenyl]ethanone

생성물 1

HCID 103989864-(3-Chloropropoxy)-3-hydroxy-alpha-methylbenzenemethanol수율 55%

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

반응 조건

온도
10 °C

실험 절차

To a flask charged with sodium borohydride (1.5 g, 39.4 mmol) under nitrogen and chilled to 10° C. was added, slowly, a solution of 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone (6.0 g, 26.2 mmol) dissolved in ethanol-tetrahydrofuran (120 ml, 2:1). After total addition, the ice bath was removed and the reaction was stirred at ambient temperature for 3 hours. An additional amount of sodium borohydride (0.2 g, 5.3 mmol) was carefully added. After stirring at ambient temperature for one hour, the solvent was removed in vacuo. The resultant solid residue was diluted with water (100 ml) and left overnight. The product was isolated by vacuum filtration yielding 3.8 g. Two consecutive recrystallizations from toluene provided 3.3 g (55%) of 4-(3-chloropropoxy)-3-hydroxy-α-methylbenzene methanol as a light brown solid, m.p.=107°-109° C.

후처리

  1. additionwas added
  2. additionAfter total addition
  3. customthe ice bath was removed
  4. stirringAfter stirring at ambient temperature for one hour
  5. customthe solvent was removed in vacuo
  6. additionThe resultant solid residue was diluted with water (100 ml)
  7. waitleft overnight
  8. customThe product was isolated by vacuum filtration
  9. customyielding 3.8 g
  10. customTwo consecutive recrystallizations from toluene

출처 및 근거

ORD 기록
ord-d6cd5509a98541a4a786b6e9688f9815
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593995

연결된 노트

불러오는 중…