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

HRID 2261436노트

반응식

HRID 2261436 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-45526604902c4452b7c4006bf0946b1c
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846964B2

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