Dimethylformamide → Benzyl 4-hydroxypentanoate

HRID 376163노트

반응식

HRID 376163 반응식
[OH:1][CH:2]([CH3:8])[CH2:3][CH2:4][C:5]([O-:7])=[O:6].[Na+].CN(C)C=O.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[OH:1][CH:2]([CH3:8])[CH2:3][CH2:4][C:5]([O:7][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:6]

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 23709111Sodium 4-hydroxypentanoate

생성물 1

HCID 18991533Benzyl 4-hydroxypentanoate수율 53.2%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

실험 절차

80 g (0.57 mol) of sodium 4-hydroxypentanoate and 184.1 g (0.57 mol) of tetrabutylammonium bromide are suspended in 1.2 liters of abs. dimethyl formamide and the suspension is stirred for 15 minutes at room temperature. Then 67.8 ml (0.57 mol) of benzyl bromide are added dropwise and the reaction mixture is stirred for 15 hours at room temperature. The solution so obtained is diluted with water and extracted three times with ether. The organic phases are washed once with water and once with brine. The combined organic phases are dried over MgSO4, filtered and concentrated by evaporation. Distillation of the residue gives 63.1 g of benzyl 4-hydroxypentanoate of b.p. 139°-140° C./2.10-2 torr as a colourless oil.

후처리

  1. customThe solution so obtained
  2. extractionextracted three times with ether
  3. washThe organic phases are washed once with water and once with brine
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. distillationDistillation of the residue

출처 및 근거

ORD 기록
ord-22b61444791249e9a20f89c41ee1e87a
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05488140

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