Ethanol → HCID 178476779, compound

HRID 482639Notes

Reaction equation

HRID 482639 reaction equation
[C:1]1([P:7](Cl)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([OH:12])[CH3:11].N1C=CC=CC=1.[OH2:19]>CCOCC>[C:1]1([PH:7](=[O:19])[O:12][CH2:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1049Pyridine2×HCID 12573Phenyl phosphorus dichloride

Product 1

HCID 178476779HCID 178476779, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of phenylphosphonous dichloride (66 g, 0.37 mol) in dry ether (100 mL) was treated dropwise with a solution of ethanol (21.6 mL, 0.37 mol) and pyridine (29.6 mL, 0.37 mol) in ether (200 mL) at room tempeature under argon. After stirring for one hour, a mixture of water (6.6 mL, 0.37 mol) and pyridine (29.6 mL) was added slowly. The reaction mixture was filtered, washed with ether, and the ether evaporated to give an oil. The oil was distilled in the Kugelrohr and then through a short Vigreux column at 95°-98° C. (0.05 mmHg); lit. (T. L. Emmick et al., J. Am. Chem. Soc., 1968, 90, 3459) 102°-103° C. (0.2 mmHg). Yield 44.3 g (70%). 1H NMR (CDCl3)δ 7.57 (d, J=569 Hz, 1H), 8.0-7.4 (m, 5H), 4.13 (2 q, JH-H =7 Hz, JP-H =14 Hz, 2H), 1.35 (t, J=7 Hz, 3H).

Workup

  1. additionwas added slowly
  2. filtrationThe reaction mixture was filtered
  3. washwashed with ether
  4. customthe ether evaporated
  5. customto give an oil
  6. distillationThe oil was distilled in the Kugelrohr
  7. customat 95°-98° C.
  8. customlit. (T. L. Emmick et al., J. Am. Chem. Soc., 1968, 90, 3459) 102°-103° C. (0.2 mmHg)

Sources & evidence

ORD record
ord-16042fe0be94458d9afe54ff61d6b922
Source dataset
uspto-grants-1986_03
Patent number
US04574060

Reaction notes

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