Benzaldehyde → HCID 53688132, compound

HRID 1982188Notes

Reaction equation

HRID 1982188 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4](P(OCC)(OCC)=O)[CH2:5][CH:6]([CH3:8])[CH3:7].[H-].[Na+].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[C:21]1([CH:20]=[C:4]([CH2:5][CH:6]([CH3:7])[CH3:8])[C:3]([O:2][CH3:1])=[O:17])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24758Sodium hydrideHCID 13653348HCID 13653348, compound

Product 1

HCID 53688132HCID 53688132, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-Methyl-2-(diethylphosphono) pentanoic acid methyl ester (25.72 g, 96.3 mmole) in dry tetrahydrofuran (250 ml) under nitrogen was added sodium hydride (4.2 g, 60% dispersion in oil) portionwise. After stirring for 30 min. at room temperature benzaldehyde (11.22 g, 96.3 mmole) was slowly added and the reaction mixture was then stirred for a further hour at room temperature. Volatiles were then removed in vacuo and the residue was dissolved in ethyl acetate, washed with saturated aqueous ammonium chloride solution (250 ml×2), dried (sodium sulphate), filtered and evaporated in vacuo to an oil. Distillation under reduced pressure gave the title compound as an oil (16.6 g, 79%); (Found: C, 75.83; H, 8.38. C14H18O2 +0.2H2O requires: C, 75.78; H, 8.36%); δ(CDCl3) 0.87 and 0.95 (together 6H, each d, each J=7 Hz, (CH3)2CH); 1.90 (1H, m, (CH3)2CH); 2.34 and 2.52 (together 2H, each d, each J=8 Hz, CH2CH(CH3 )2); 3.82 (3H, s, OCH3); 7.70 and 7.2-7.42 (together 6H, s, m, C6H5, vinyl CH).

Workup

  1. additionwas slowly added
  2. customVolatiles were then removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous ammonium chloride solution (250 ml×2)
  5. dry with materialdried (sodium sulphate)
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil
  8. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-a9851f87676b4e9f9f9300f7bdd5952b
Source dataset
uspto-grants-1986_06
Patent number
US04595700

Reaction notes

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