Dimethylformamide → Benzyl 4-hydroxypentanoate

HRID 487497Notes

Reaction equation

HRID 487497 reaction equation
[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]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 23709111Sodium 4-hydroxypentanoate

Product 1

HCID 18991533Benzyl 4-hydroxypentanoateYield 53.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5834a9db422d4279a6b0e725419bf31e
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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