Potassium Carbonate → HCID 12388107, compound

HRID 919105Notes

Reaction equation

HRID 919105 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([OH:3])=[O:2].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:7]/[C:6]1[CH:5]=[C:4]([CH:11]=[CH:10][CH:9]=1)[C:1]([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120773-CarboxybenzaldehydeHCID 80029Trimethyl phosphonoacetate

Product 1

HCID 12388107HCID 12388107, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

3-Carboxybenzaldehyde (25 g, 0.167 mol) and K2CO3 (69 g, 0.499 mol) were added to water (250 mL) and cooled to 0-5° C. Trimethyl phosphonoacetate (32.3 mL, 0.2 mol) was charged dropwise maintaining the reaction temperature below 15° C. The reaction was warmed and stirred at RT for 17 h. The mixture was acidified to pH ˜1, filtered and dried in vacuo to afford the product as an off-white solid (37.25 g, >100%—slightly wet). 1H NMR (300 MHz, CD3OD) δ: 8.23 (1H, s), 8.06 (1H, d, J=7.8 Hz), 7.86 (1H, d, J=7.5 Hz), 7.75 (1H, d, J=15.9 Hz), 6.61 (1H, d, J=16.2 Hz), 7.54 (1H, t), 3.81 (3H, s).

Workup

  1. temperaturemaintaining the reaction temperature below 15° C
  2. temperatureThe reaction was warmed
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-18dc2172bcae48d68a11509308e25e38
Source dataset
uspto-grants-2016_03
Patent number
US09273003B2

Reaction notes

Loading…