Benzene → 2-(2-methylpropanoyloxy)ethyl 2-methylpropanoate

HRID 2254354Notes

Reaction equation

HRID 2254354 reaction equation
C(O)[CH2:2][CH2:3][OH:4].C1C=CC=CC=1.[C:12]([OH:17])(=[O:16])[CH:13]([CH3:15])[CH3:14].[OH2:18].[C:19]1([CH3:29])[CH:24]=CC(S(O)(=O)=O)=C[CH:20]=1>O>[CH3:14][CH:13]([CH3:15])[C:12]([O:17][CH2:2][CH2:3][O:4][C:24](=[O:18])[CH:19]([CH3:20])[CH3:29])=[O:16]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6590Isobutyric AcidHCID 104421,3-PropanediolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 2442882-(2-methylpropanoyloxy)ethyl 2-methylpropanoateYield 850.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 28.0 ml (31.0 g, 0.5 mole) of ethylene glycol (VIII), 200 ml of benzene, 111.6 ml (105.8 g, 1.2 mole) of isobutyric acid and 9.5 g (0.05 mole) of p-toluenesulfonic acid monohydrate is stirred under reflux for 2.5 hours, while the water being formed is continuously separated by using a Dean-Stark apparatus. Then the mixture is cooled to about 10° C., extracted three times with 100 ml of ice-cold 1N aqueous sodium hydroxide solution, washed with water until neutral, dried over sodium sulfate and the solvent is distilled off under reduced pressure. The crude product obtained in almost quantitative yield is subjected to fractional distillation under reduced pressure. Thus 86.0 g of the desired compound are obtained in the form of a colourless oil. Yield: 85.0 %. B.p.: 74°-76° C./107 Pa. According to gas-chromatography the product is homogeneous and contains 0.3% by weight of water (determined according to Karl Fisher's method). The product thus obtained can be used directly in the next reaction step.

Workup

  1. customformed
  2. customis continuously separated
  3. extractionextracted three times with 100 ml of ice-cold 1N aqueous sodium hydroxide solution
  4. washwashed with water until neutral,
  5. dry with materialdried over sodium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customThe crude product obtained in almost quantitative yield
  8. distillationis subjected to fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-4f248dfbc1ae4fa09cf3754b82157ab5
Source dataset
uspto-grants-1993_08
Patent number
US05235097

Reaction notes

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