Methyl iodide → Phenylpropynoic acid methyl ester

HRID 2410654Notes

Reaction equation

HRID 2410654 reaction equation
[C:1](O)(=O)C#C.[C:6]1([C:12]#[C:13][C:14]([OH:16])=[O:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CI.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:6]1([C:12]#[C:13][C:14]([O:16][CH3:1])=[O:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 10110Propiolic AcidHCID 11430Potassium CarbonateHCID 69475Phenylpropiolic Acid3×

Product 1

HCID 138378Phenylpropynoic acid methyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Typical Procedure for Methylation of Propiolic Acid with Iodomethane (1b as Example) CH3I (2.2 mmol) and K2CO3 (2.2 mmol) were added to the solution of Propiolic acid (1b, 2 mmol) in acetonitrile and the obtained mixture was stirred at room temperature. The reaction was monitored by TLC until the starting 1b disappeared. After 3 hours, the mixture was extracted with ether (3×5 mL). The combined ether part was purified by column chromatography on silica gel (dichloromethane:hexane=1:3) to give pure methyl 3-phenylpropiolate in 98% yield. GC/Ms: m/z: 160. Data for 1H and 13C NMR of methyl 3-phenylpropiolate was conducted in CDCl3 and consistent with the data in reported literature.

Workup

  1. extractionthe mixture was extracted with ether (3×5 mL)
  2. customThe combined ether part was purified by column chromatography on silica gel (dichloromethane:hexane=1:3)

Sources & evidence

ORD record
ord-edd1b316e5334a57948ae5d0e9f5e96a
Source dataset
uspto-grants-2014_08
Patent number
US08816127B2

Reaction notes

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