Methanol → HCID 54264503, compound

HRID 1241603Notes

Reaction equation

HRID 1241603 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])[CH:4]=[N:3]1.S(=O)(=O)(O)O.[OH-].[Na+].[CH3:19]O>>[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=[CH:8][C:9]([O:11][CH3:19])=[O:10])[CH:4]=[N:3]1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 592440HCID 592440, compound

Product 1

HCID 54264503HCID 54264503, compound

Procedure

3-(1-Methylpyrazol-4-yl)acrylic acid (86.8 g) was added to a solution of sulphuric acid (20 ml) in methanol (690 ml), and the mixture refluxed for 2.5 hours, cooled, then poured onto ice. The acid was neutralised with aqueous sodium hydroxide and the product extracted into dichloromethane, which was dried and evaporated. Crystallisation from ether/petrol gave methyl 3-(1-methylpyrazol-4-yl)acrylate (89.0 g). 1H-NMR (d6-DMSO) δ 3.77 (3H,s), 3.91 (3H,s), 6.16 (1H,d), 7.54 (1H,s), 7.56 (1H,d), 7.69 (1H,s). (APCI) found (M+H)=167. C8H10N2O2 requires 166.

Workup

  1. temperaturethe mixture refluxed for 2.5 hours
  2. temperaturecooled
  3. additionpoured onto ice
  4. extractionthe product extracted into dichloromethane, which
  5. customwas dried
  6. customevaporated
  7. customCrystallisation from ether/petrol

Sources & evidence

ORD record
ord-bf5a101ed2c74125ae4f21d014e383df
Source dataset
uspto-grants-2006_10
Patent number
US07115616B2

Reaction notes

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