1-Butanol → Butanedioic acid, 2-hydroxy-, 1,4-dibutyl ester

HRID 641127Notes

Reaction equation

HRID 641127 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[CH:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[OH:3].C(O)[CH2:13][CH2:14][CH3:15].[C:17]1(C)[CH:22]=CC(S(O)(=O)=O)=C[CH:18]=1>C(OCC)(=O)C>[C:1]([O:10][CH2:11][CH2:18][CH2:17][CH3:22])(=[O:9])[CH:2]([CH2:4][C:5]([O:7][CH2:8][CH2:13][CH2:14][CH3:15])=[O:6])[OH:3]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 12674Dimethyl malate

Product 1

HCID 95385Butanedioic acid, 2-hydroxy-, 1,4-dibutyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

A 100 mL three-neck flask, equipped with a magnetic stir bar, a Claisen adapter with a thermocouple and a nitrogen inlet, and a short path condenser, was charged with 4.45 grams of dimethyl malate, 40 mL 1-butanol, and 0.51 gram of p-toluenesulfonic acid. The reaction was stirred at 115° C. for 3.7 hours with a nitrogen sweep. The reaction mixture was taken up in ethyl acetate, extracted with dilute aqueous sodium bicarbonate, washed three times with water, dried over magnesium sulfate, and filtered. Solvent was removed by rotary evaporation to yield 6.8 grams of a straw-colored liquid.

Workup

  1. customA 100 mL three-neck flask, equipped with a magnetic stir bar
  2. extractionextracted with dilute aqueous sodium bicarbonate
  3. washwashed three times with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customSolvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-545892f8d2c44cf7b07d812ee05f827a
Source dataset
uspto-grants-2010_04
Patent number
US07696136B2

Reaction notes

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