1-Butanol → Dibutyl squarate

HRID 1651424Notes

Reaction equation

HRID 1651424 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[C:6]1([CH3:12])[CH:11]=[CH:10]C=CC=1.[OH:13][C:14]1[C:17](=O)[C:16](=[O:19])[C:15]=1[OH:20]>O>[CH2:1]([O:5][C:17]1[C:14](=[O:13])[C:15](=[O:20])[C:16]=1[O:19][CH2:10][CH2:11][CH2:6][CH3:12])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 1140TolueneHCID 17913Squaric acid

Product 1

HCID 65108Dibutyl squarate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Protected by a nitrogen atmosphere, a mixture of 1-butanol (64 mL), toluene (42 mL), and 1,2-dihydroxy-1-cyclobutene-3,4-dione (21.43 g, 0.1878 mole) was heated under reflux with stirring under a Dean-Stark water separator until water stopped passing over (7.6 mL of water was collected). Reflux was continued for a further 30 minutes, then the excess toluene and butanol were distilled off under reduced pressure (50-100 mm Hg) to give the title compound as a yellow liquid. The concentrate was diluted with 25 mL of methanol.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customstopped passing over (7.6 mL of water was collected)
  4. temperatureReflux
  5. distillationthe excess toluene and butanol were distilled off under reduced pressure (50-100 mm Hg)

Sources & evidence

ORD record
ord-257422e46ae440279540e8146a74b5a2
Source dataset
uspto-grants-1990_05
Patent number
US04927970

Reaction notes

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