Methanol → HCID 86594299, compound

HRID 1988125Notes

Reaction equation

HRID 1988125 reaction equation
C1(C)C=CC=CC=1.[C:8]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)(=O)[CH3:9].C[OH:17].[C:18](=O)([O:21]C)[O:19][CH3:20]>>[O:17]=[CH:9][CH:8]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[C:18]([O:19][CH3:20])=[O:21]

Participants

5

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 69202-AcetylthiopheneHCID 12021Dimethyl Carbonate2×

Product 1

HCID 86594299HCID 86594299, compound

Procedure

510 ml of dimethyl carbonate and 1 500 ml of toluene were heated to 100° C. in a 2 L flask and a solution of 257 g of 2-acetylthiophene in 510 ml of dimethyl carbonate was then added dropwise within the space of 4 hours. The methanol which was formed in the reaction was distilled off as an azeotrope. 120 ml of conc. sulphuric acid were introduced, in 900 g of ice, into a 4 L flask and the cooled reaction mixture was added such that 40° C. was not exceeded. The mixture was then stirred and the pH was adjusted to pH 1. The phases were separated and the organic phase was extracted three times by shaking with an aqueous solution of sodium sulphate and then concentrated in vacuo. Vacuum distillation of the crude product yielded 278 g of methyl 3-oxo-(2-thiophenyl)propanoate as a transparent, slightly yellowish liquid (98% pure according to GC, 74% of theory).

Workup

  1. distillationwas distilled off as an azeotrope
  2. addition120 ml of conc. sulphuric acid were introduced, in 900 g of ice, into a 4 L flask
  3. customthe cooled reaction mixture
  4. additionwas added such that 40° C.
  5. customThe phases were separated
  6. extractionthe organic phase was extracted three times
  7. stirringby shaking with an aqueous solution of sodium sulphate
  8. concentrationconcentrated in vacuo
  9. distillationVacuum distillation of the crude product

Sources & evidence

ORD record
ord-b2e108286cc2435fb338e317da5b51e8
Source dataset
uspto-grants-2009_06
Patent number
US07553970B2

Reaction notes

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