Hydrochloric Acid → HCID 54303311, compound

HRID 1976611Notes

Reaction equation

HRID 1976611 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].[H-].[Na+].P(=O)([O-])[O-:15].Cl.[O:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>O>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:21][C:20]([O:19][CH2:23][CH3:22])=[O:15])=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 406CID 406HCID 8028Tetrahydrofuran2×HCID 120884-Formylbenzoic acidHCID 24758Sodium hydride2×

Product 1

HCID 54303311HCID 54303311, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Carboxybenzaldehyde (1.0 g) was added to sodium hydride (170 mg) in 100 mL tetrahydrofuran at 0° C. In a separate flask, triethyl phosphonoacetate (1.60 mL) was added to sodium hydride (200 mg) in 100 mL tetrahydrofuran at 0° C. The phosphonate anion solution was cannulated into the slurry of the carboxylate anion and the resulting thick white slurry was stirred for 16 hours. Water (50 mL) was added followed by concentrated hydrochloric acid until the pH was 1. The precipitate was collected by filtration, dissolved in ether and dried with magnesium sulfate. Evaporation under reduced pressure gave the product (1.47 g; 100%) as a white solid.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. dissolutiondissolved in ether
  3. dry with materialdried with magnesium sulfate
  4. customEvaporation under reduced pressure
  5. customgave the product (1.47 g; 100%) as a white solid

Sources & evidence

ORD record
ord-41653a936d434b42a91dcee5c3b7995d
Source dataset
uspto-grants-2001_05
Patent number
US06228872B1

Reaction notes

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