Neopentyl alcohol → HCID 9942177, compound

HRID 1457376Notes

Reaction equation

HRID 1457376 reaction equation
[CH2:1]([OH:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:7](=O)([O:10]C)[O:8][CH3:9]>C[O-].[Na+].CO>[C:7](=[O:10])([O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])[O:8][CH3:9]

Participants

4

Conditions

Temperature
100 °C

Procedure

To a mixed solution of neopentyl alcohol (500 ml, 5.7 mol) and dimethyl carbonate (2070 g, 23.0 mol), a 28% sodium methoxide/methanol solution (11 g) was added and the mixture was heated to 100° C. to remove the methanol by evaporation for 6 hours. After allowing the mixture to cool to room temperature, an aqueous solution of ammonium chloride was added to the mixture and the mixture was shaken to remove the sodium methoxide. The organic layer was washed with water, dried and distilled to give methyl neopentyl carbonate as a colorless liquid (450 g, yield 55%). The chemical structure of the produced compound was determined based on the IR and NMR absorbance spectra shown in FIG. 1 and FIG. 2 respectively and the mass spectrometry spectrum (M/e=146).

Workup

  1. customto remove the methanol
  2. customby evaporation for 6 hours
  3. temperatureto cool to room temperature
  4. additionan aqueous solution of ammonium chloride was added to the mixture
  5. customto remove the sodium methoxide
  6. washThe organic layer was washed with water
  7. customdried
  8. distillationdistilled

Sources & evidence

ORD record
ord-be4aedcb63f84b42a587edc2da787b70
Source dataset
uspto-grants-1998_12
Patent number
US05847188

Reaction notes

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