Diisopropylethylamine → 3-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid

HRID 1665907노트

반응식

HRID 1665907 반응식
[CH:1]([C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[C:5]([CH3:15])[CH:4]=1)=[O:2].CCN(C(C)C)C(C)C>C(O)C.[Pd]>[OH:2][CH2:1][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:5]([CH3:15])[CH:4]=1

참가 물질

5

반응물 2

HCID 81531DiisopropylethylamineHCID 765393083-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid

생성물 1

HCID 574374033-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid수율 97.8%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a solution of 3-(4-formyl-2,6-dimethyl-phenyl)-acrylic acid (2.2 g, 10.8 mmol) and DIPEA (2.0 mL, 11.9 mmol) in ethanol (80 mL), Pd/C (200 mg, 10% Pd, moistened with 50% water) is added. The suspension is vigorously stirred under 1 bar of H2 for 1 h. The mixture is filtered over Celite and the filtrate is evaporated. The residue is poured onto 1 N aq. HCl/ice and extracted with EA. The organic extract is washed once with 1 N aq. HCl and once with brine, dried over MgSO4, filtered and evaporated to give 3-(4-hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid (2.2 g) as a pale yellow resin; LC-MS: tR=0.71 min.

후처리

  1. filtrationThe mixture is filtered over Celite
  2. customthe filtrate is evaporated
  3. additionThe residue is poured onto 1 N aq. HCl/ice
  4. extractionextracted with EA
  5. extractionThe organic extract
  6. washis washed once with 1 N aq. HCl and once with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-5a8566a1e781496cb6970d241c69b539
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039644B2

반응 노트

불러오는 중…