Potassium Carbonate → 4-((1E)-3-methoxy-3-oxoprop-1-en-1-yl)benzoic acid

HRID 475040Notes

Reaction equation

HRID 475040 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=O.C([O-])([O-])=O.[K+].[K+].[CH3:18][O:19][C:20]([CH2:22]P(OC)(OC)=O)=[O:21]>O>[CH3:18][O:19][C:20](=[O:21])/[CH:22]=[CH:1]/[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120884-Formylbenzoic acidHCID 80029Trimethyl phosphonoacetate

Product 1

HCID 106083304-((1E)-3-methoxy-3-oxoprop-1-en-1-yl)benzoic acidYield 107.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

4-Formylbenzoic acid (20 g, 0.133 mol) and K2CO3 (55 g, 0.398 mol) were added to water (350 mL) and cooled to 0-5° C. Trimethyl phosphonoacetate (26 mL, 0.160 mol) was charged dropwise maintaining the reaction temperature below 15° C. The reaction was then warmed and stirred at RT for 1.5 h before acidifying to pH˜1. The resulting precipitate was filtered and dried in vacuo to afford the title product as a pale yellow solid (29.5 g, quant). 1H NMR (300 MHz, d6-DMSO) δ: 7.89-7.52 (5H, m), 6.59 (1H, d, J=16.2 Hz), 3.7 (3H, s).

Workup

  1. temperaturemaintaining the reaction temperature below 15° C
  2. temperatureThe reaction was then warmed
  3. filtrationThe resulting precipitate was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-0cdae13231b049fdb1229ef5275b1c9f
Source dataset
uspto-grants-2014_01
Patent number
US08637547B2

Reaction notes

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