Aluminium lithium hydride → 3-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propan-1-ol

HRID 1665909노트

반응식

HRID 1665909 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][CH2:17][C:18](O)=[O:19])=[C:11]([CH3:21])[CH:10]=1>C1COCC1>[OH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][CH2:17][CH2:18][OH:19])=[C:11]([CH3:21])[CH:10]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydride2회HCID 574374033-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid

생성물 1

HCID 574374073-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propan-1-ol수율 98.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of LiAlH4 (219 mg, 5.76 mmol) in THF (35 mL), a solution of 3-(4-hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid (1.0 g, 4.80 mmol, intermediate from Aldehyde 4) in THF (10 mL) is added dropwise. Upon complete addition the suspension is refluxed for 2 h. The suspension is diluted with THF (10 mL) and another portion of LiAlH4 (182 mg, 4.80 mmol) is added. The mixture is refluxed for further two hours, then cooled with an ice-bath. The reaction is carefully quenched by adding sat. aq. NH4Cl solution (2 mL) followed by 2 N aq. HCl until a clear solution forms. The mixture is diluted with water and extracted twice with EA. The combined organic extracts are dried over MgSO4, filtered and the solvent of the filtrate is evaporated to leave 3-(4-hydroxymethyl-2,6-dimethyl-phenyl)-propan-1-ol (920 mg) as a colourless crystalline solid; LC-MS: tR=0.70 min, [M+1−H2O]+=177.20.

후처리

  1. additionUpon complete addition the suspension
  2. temperatureis refluxed for 2 h
  3. temperatureThe mixture is refluxed for further two hours
  4. temperaturecooled with an ice-bath
  5. customThe reaction is carefully quenched
  6. additionby adding sat. aq. NH4Cl solution (2 mL)
  7. additionThe mixture is diluted with water
  8. extractionextracted twice with EA
  9. dry with materialThe combined organic extracts are dried over MgSO4
  10. filtrationfiltered
  11. customthe solvent of the filtrate is evaporated

출처 및 근거

ORD 기록
ord-5e1a6905a24d4c399fbc6d5ab78d85a5
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039644B2

반응 노트

불러오는 중…