Potassium Carbonate → Sodium 2-(2-methoxycarbonyl-vinyl)benzenesulfonate

HRID 351069Notes

Reaction equation

HRID 351069 reaction equation
O.[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([O-:13])(=[O:12])=[O:11])=O.[Na+:14].C(=O)([O-])[O-].[K+].[K+].[CH3:21][O:22][C:23]([CH2:25]P(OC)(OC)=O)=[O:24]>O>[CH3:21][O:22][C:23]([CH:25]=[CH:2][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([O-:13])(=[O:12])=[O:11])=[O:24].[Na+:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 80029Trimethyl phosphonoacetateHCID 16211671Sodium 2-formylbenzene-1-sulfonate--water (1/1/1)

Product 1

HCID 74088446Sodium 2-(2-methoxycarbonyl-vinyl)benzenesulfonateYield 52.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of sodium 2-formylbenzenesulfonate hydrate (31) (tech., purity 75%; 1.33 g, 4.79 mmol), potassium carbonate (1.32 g, 9.56 mmol), and trimethyl phosphonoacetate (1.05 g, 5.77 mmol) in water (2.5 ml) was vigorously stirred at ambient temperature for 1 hour. The precipitate was filtered and carefully washed with methanol. The methanol extract was evaporated to give the title compound (0.66 g, 52%) as a white solid. 1H NMR (DMSO-d6, HMDSO), δ: 3.72 (3H, s); 6.43 (1H, d, J=16.0 Hz); 7.18–7.96 (4H, m); 8.83 (1H, d, J=16.0 Hz).

Workup

  1. filtrationThe precipitate was filtered
  2. washcarefully washed with methanol
  3. extractionThe methanol extract
  4. customwas evaporated

Sources & evidence

ORD record
ord-bc418f3bb7f24c07b6a83e5ef1f410e3
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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