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

HRID 55601

反応式

HRID 55601 の反応式
[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]

参加物

4

反応物 2

HCID 4311764Sodium borohydride2 回HCID 103765071-(4-(3-Chloropropoxy)-3-hydroxyphenyl]ethanone

生成物 1

HCID 103989864-(3-Chloropropoxy)-3-hydroxy-alpha-methylbenzenemethanol収率 55%

試薬・触媒・溶媒 1

HCID 21873804Tetrahydrofuran ethanol溶媒

反応条件

温度
10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-31eb0799bcf44dfc8bc8c8d6a7abf5b5
出典データセット
uspto-grants-1997_04
特許番号
US05624927

関連ノート

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