Potassium Carbonate → Methane

HRID 1413050Notes

Reaction equation

HRID 1413050 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:8][CH:9](OCC)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)C.CC1C=CC(COC(NNC(C2[CH:43]=[N:42][CH:41]=CN=2)=O)=O)=CC=1.[C:44](=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1.CN(C)C=O>[CH4:6].[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:10](=[CH:41][N:42]([CH3:43])[CH3:44])[CH:9]=[O:8])=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 2513151-(2,2-Diethoxyethoxy)-4-methoxybenzeneHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamate

Product 2

HCID 297MethaneHCID 544980242-(p-Methoxyphenoxy)-3-(dimethylamino)acrolein

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Dry dimethylformamide (20 ml) was added dropwise to a stirred solution of phosphorus oxychloride (18 ml) maintained at a remperature of 0° C. The reaction mixture was allowed to warm to room temperature and p-methoxyphenoxyacetaldehyde diethyl acetal (16 g) was added with stirring. The mixture was cautiously heated with stirring to a temperature of 90° C. and then maintained at that temperature for 6 hr. The mixture was then cooled and poured slowly onto crushed ice (c. 1 kg) and the pH of the solution adjusted to pH10 by the addition, with stirring, of solid potassium carbonate. A benzene (95%)/alcohol (5%) solution (500 ml) was added to the reaction mixture and the total mixture heated just below its boiling point for 2 hr. The mixture was cooled, the organic layer was separated and dried, and the solvent removed by distillation under reduced pressure to give a black oil. The product crystallised from ethanol, after treatment with charcoal, to give 2-(p-methoxyphenoxy)-3-(dimethylamino)-acrolein (6.4 g) which was characterised by p.m.r. spectroscopy.

Workup

  1. temperatureto warm to room temperature
  2. temperatureThe mixture was cautiously heated
  3. stirringwith stirring to a temperature of 90° C.
  4. temperaturemaintained at that temperature for 6 hr
  5. temperatureThe mixture was then cooled
  6. additionpoured slowly
  7. temperaturethe total mixture heated just below its boiling point for 2 hr
  8. temperatureThe mixture was cooled
  9. customthe organic layer was separated
  10. customdried
  11. customthe solvent removed by distillation under reduced pressure
  12. customto give a black oil
  13. customThe product crystallised from ethanol

Sources & evidence

ORD record
ord-23981861004f46439e6b3bde4d86c737
Source dataset
uspto-grants-1981_02
Patent number
US04248618

Reaction notes

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