1-Butanol → Dibutyl maleate

HRID 1112610Notes

Reaction equation

HRID 1112610 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[OH2:8].[CH2:9](O)[CH2:10][CH2:11][CH3:12]>>[C:4]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])(=[O:8])/[CH:3]=[CH:2]\[C:1]([O:6][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 962WaterHCID 7923Maleic Anhydride

Product 1

HCID 5271569Dibutyl maleate

Procedure

Seventy grams (0.63 mole) maleic anhydride is dissolved in 300 mls n-butanol containing one gram p-toluene sulfonic acid. The solution is refluxed for 16 hours during which the water formed is removed with a Dean Stark trap. The excess butanol is then distilled in vacuo to give a residue of 200 g of dibutyl maleate (structure verified by NMR analysis).

Workup

  1. customformed
  2. customis removed with a Dean Stark trap
  3. distillationThe excess butanol is then distilled in vacuo

Sources & evidence

ORD record
ord-2af99839466d4d929f4bafdfcdec00c8
Source dataset
uspto-grants-1978_10
Patent number
US04123459

Reaction notes

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