Butyl pent-3-enoate → HCID 21282404, compound

HRID 414360Notes

Reaction equation

HRID 414360 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][O-:5].[Na+].[C:7]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:12])[CH2:8][CH:9]=[CH:10][CH3:11]>C(O)CCC>[CH2:4]([O:5][CH:9]([CH2:10][CH3:11])[CH2:8][C:7]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[CH2:3][CH2:2][CH3:1]

Participants

4

Reactant 2

HCID 140615Butyl pent-3-enoateHCID 23669364Sodium n-butylate

Product 1

HCID 21282404HCID 21282404, compoundYield 825.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 4.8 g of sodium butylate in 74 g of n-butanol was added to 156 g of n-butyl 3-pentenoate at room temperature, and the mixture was heated to 65° C. and stirred at this temperature for 6 hours. The reaction mixture was cooled, n-butanol was distilled off, the residue was extracted by shaking with 25 ml of water, and the organic phase was dried over Na2SO4. Fractional distillation gave 95 g (41% of theory) of n-butyl 3-n-butoxyvalerate.

Workup

  1. temperatureThe reaction mixture was cooled
  2. distillationn-butanol was distilled off
  3. extractionthe residue was extracted
  4. stirringby shaking with 25 ml of water
  5. dry with materialthe organic phase was dried over Na2SO4
  6. distillationFractional distillation

Sources & evidence

ORD record
ord-60523c08ec49417083d40907513c0c0e
Source dataset
uspto-grants-1988_12
Patent number
US04791219

Reaction notes

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