Ammonium Chloride → 3-(4-Hydroxymethyl-phenyl)-propan-1-OL

HRID 2261436ノート

反応式

HRID 2261436 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](O)=[O:18])=[CH:11][CH:10]=1.[NH4+].[Cl-]>C1COCC1>[OH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][OH:18])=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 203221243-[4-(Hydroxymethyl)phenyl]propanoic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 112406973-(4-Hydroxymethyl-phenyl)-propan-1-OL収率 76.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

To a suspension of LiAlH4 (155 mg, 4.0 mmol) in THF (25 mL) a solution of 3-(4-hydroxymethyl-phenyl)-propionic acid (720 mg, 4.0 mmol) in THF (20 mL) is added within 2 min. The resulting mixture is stirred at 70° C. for 80 min before it is treated with sat. aq. NH4Cl solution (10 mL). The suspension is filtered over celite, the filtrate is diluted with water (200 mL) and extracted with diethyl ether (2×75 mL) followed by EA (2×75 mL). The organic extracts are combined, dried over Na2SO4 and evaporated to leave 3-(4-hydroxymethyl-phenyl)-propan-1-ol (0.51 g) as a colourless oil; tR=0.61 min.

後処理

  1. additionis added within 2 min
  2. filtrationThe suspension is filtered over celite
  3. additionthe filtrate is diluted with water (200 mL)
  4. extractionextracted with diethyl ether (2×75 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated

出典と根拠

ORDレコード
ord-45526604902c4452b7c4006bf0946b1c
出典データセット
uspto-grants-2010_12
特許番号
US07846964B2

反応ノート

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