Dimethyl Carbonate → HCID 54085953, compound

HRID 622622Notes

Reaction equation

HRID 622622 reaction equation
[C:1](=O)([O:4]C)[O:2][CH3:3].C[O-].[Na+].[CH2:10]=[C:11]([OH:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[C:1](=[O:4])([O:2][CH3:3])[O:19][CH:11]([CH3:10])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 10942334Sodium MethoxideHCID 120571223-Phenylprop-1-en-2-ol2×

Product 1

HCID 54085953HCID 54085953, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
78 °C

Procedure

Into a 2 liter reaction flask equipped with stirrer, thermometer, reflux condenser, heating mantle and Bidwell addition funnel is placed 222 grams of dimethyl carbonate and 24 grams of a solution of sodium methoxide in methanol. The resulting mixture is heated to reflux. Over a 30 minute period 268 grams of alpha-methylene phenylethyl alcohol having the structure: ##STR161## is added over a period of 20 minutes after bringing the mixture to reflux at 72°-76° C. At the end of the addition of the alpha-methylene phenylethyl alcohol the reaction mass is continued to be refluxed at 78° C. for a period of two hours. At the end of the two hour period, the excess methyl alcohol is taken off at 100° C. The reaction mass is then cooled and 200 ml wter is added thereto. The organic phase is then distilled on a 12" Goodloe column yielding the following fractions:

Workup

  1. customInto a 2 liter reaction flask
  2. customequipped with stirrer
  3. temperaturethermometer, reflux condenser
  4. temperatureheating mantle
  5. additionBidwell addition funnel
  6. temperatureThe resulting mixture is heated to reflux
  7. addition##STR161## is added over a period of 20 minutes
  8. temperatureto reflux at 72°-76° C
  9. customAt the end of the two hour period
  10. customis taken off at 100° C
  11. temperatureThe reaction mass is then cooled
  12. addition200 ml wter is added
  13. distillationThe organic phase is then distilled on a 12" Goodloe column
  14. customyielding the following fractions

Sources & evidence

ORD record
ord-f3c6bc51db8343dd9939daeed9ee28dd
Source dataset
uspto-grants-1988_09
Patent number
US04772583

Reaction notes

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