1-Butanol → Dibutyl squarate

HRID 1651420Notes

Reaction equation

HRID 1651420 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

A mixture of 1-butanol (48 mL), toluene (32 mL), and 1,2-dihydroxy-l-cyclobutene-3,4-dione (16.0 g, 0.1402 mole) was heated at reflux under a nitrogen atmosphere with stirring under a Dean-Stark water separator until water stopped passing over. The resulting solution of the title compound was cooled to 0°-5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere

Sources & evidence

ORD record
ord-770caf9668ec460cb8c845c12d78acd7
Source dataset
uspto-grants-1990_05
Patent number
US04927970

Reaction notes

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