Ethanol → Ethyl diphenylphosphinite

HRID 1380386Notes

Reaction equation

HRID 1380386 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].N1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:19]COCC>>[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:12][CH2:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 3283Diethyl EtherHCID 12573Phenyl phosphorus dichloride

Product 1

HCID 69754Ethyl diphenylphosphinite

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) 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) 102103° C. (0.2 mmHg). Yield 44.3 g (70%). 1H NMR (CDCl3) δ 7.57 (d, J=569 Hz, 1 H), 8.0-7.14 (m, 5 H), 4.13 (2 q, JH--H =7 Hz, JP-H =14 Hz, 2 H), 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) 102103° C. (0.2 mmHg)

Sources & evidence

ORD record
ord-4f838edf2d954951bf8b053bd3c115eb
Source dataset
uspto-grants-1986_04
Patent number
US04581415

Reaction notes

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