Methanol → HCID 57265114, compound

HRID 1525471Notes

Reaction equation

HRID 1525471 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[CH2:3][CH:4]([C:10]([O:12]CC)=[O:11])[C:5]([O:7]CC)=[O:6].CO.[OH-].[K+].C1(C)C=CC=CC=1>O>[CH3:1][C:2]([CH3:16])([CH3:15])[CH2:3][CH:4]([C:5]([OH:7])=[O:6])[C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 14797Potassium HydroxideHCID 250882diethyl(2,2-dimethylpropyl)propanedioate

Product 1

HCID 57265114HCID 57265114, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the above-obtained diethyl (2,2-dimethylpropyl)malonate on 500 cm3 of methanol a solution of 125 g of KOH in 1000 cm3 of water was added. The obtained mixture was refluxed for 5 h, and then methanol and ethanol were distilled off at atmospheric pressure. To the residue ca. 3000 cm3 of water was added, the obtained solution was acidified by saturated HCl to pH 1. The formed product was extracted with 3×500 ml of ether. To the combined extract 200 ml of toluene was added, and the obtained solution was evaporated in vacuum to give a ca. 3 to 1 mixture of the title product and toluene (on the evidence of NMR spectroscopy). This mixture was further used without an additional purification.

Workup

  1. temperatureThe obtained mixture was refluxed for 5 h
  2. distillationmethanol and ethanol were distilled off at atmospheric pressure
  3. additionTo the residue ca. 3000 cm3 of water was added
  4. extractionThe formed product was extracted with 3×500 ml of ether
  5. extractionTo the combined extract 200 ml of toluene
  6. additionwas added
  7. customthe obtained solution was evaporated in vacuum
  8. customto give a ca. 3

Sources & evidence

ORD record
ord-fe087f45bb9a4540aca797949f8d33c3
Source dataset
uspto-grants-2015_07
Patent number
US09079985B2

Reaction notes

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