Benzaldehyde → 6329-46-0

HRID 1056869Notes

Reaction equation

HRID 1056869 reaction equation
[P:1]([O-:6])([O:4][CH3:5])[O:2][CH3:3].[CH:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F-].[K+]>C(Cl)Cl>[OH:14][CH:7]([P:1](=[O:6])([O:4][CH3:5])[O:2][CH3:3])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 522689Potassium FluorideHCID 21884954Dimethylphosphite

Product 1

HCID 2388826329-46-0Yield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethyl phosphite (1.86 mL, 20.3 mmol, 1.03 eq) was added to benzaldehyde (2 mL, 19.8 mmol, 1 eq) and stirred for 5 min. KF (5.75 g, 99.0 mmol, 5 eq) was then added and the reaction mixture was stirred until it solidified (˜20 min). The crude product was then dissolved in DCM, filtered, and the solvent evaporated yielding 4 as a white powder (4.38 g, 100%). The product was dried under high vacuum over P2O5. No further purification was required. 1H NMR (400 MHz CDCl3) δ 7.53-7.45 (m, 2H), 7.43-7.23 (m, 3H), 5.05 (d, J=11.1 Hz, 1H), 3.67 (dd, J=14.3, 10.4 Hz, 6H). 13C NMR (101 MHz, CDCl3) δ 136.66 (s), 128.64 (s), 128.49 (s), 127.28 (d, JC-P=5.7 Hz), 70.86 (d, JC-P=159.6 Hz), 54.02 (dd, JC-P=28.4, 7.0 Hz). 31P NMR (162 MHz CDCl3) δ 24.71 (s). ESIMS calculated for C9H13O4PNa [M+Na]+239.06, found: 239.04; mp 85-86° C.

Workup

  1. stirringthe reaction mixture was stirred until it
  2. custom(˜20 min)
  3. filtrationfiltered
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-22740d80cdd74780a26a81194641a6d5
Source dataset
uspto-grants-2016_07
Patent number
US09399653B2

Reaction notes

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