1-Butanol → Dibutyl squarate

HRID 1651429Notes

Reaction equation

HRID 1651429 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 962WaterSolvent

Procedure

A mixture of 1-butanol (3 L), toluene (2 L) and 1,2-dihydroxy-1-cyclobutene-3,4-dione (1 kg; 8.767 moles) was refluxed with stirring under a Dean-Stark separator until water stopped passing over (theory:0.316 L). The excess toluene and butanol were then removed by distillation under reduced pressure to give the title compound as a yellow liquid. The concentrate was diluted with methanol (1.5L) and used in the next step.

Workup

  1. temperaturewas refluxed
  2. customThe excess toluene and butanol were then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-3ebd215017114a43be5392fae4de2ba1
Source dataset
uspto-grants-1990_05
Patent number
US04927970

Reaction notes

Loading…