Benzyl Alcohol → HCID 59717679, compound

HRID 1863191Notes

Reaction equation

HRID 1863191 reaction equation
[CH3:1][P:2](Cl)([CH3:4])=[O:3].[CH2:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[CH3:1][P:2]([CH3:4])(=[O:3])[O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 517954Dimethylphosphinic chloride

Product 1

HCID 59717679HCID 59717679, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0°) solution of dimethylphosphinyl chloride (3.4 g., 0.03 moles) in dichloromethane (50 ml.) is added dropwise (over a period of 20 minutes), with stirring, a solution of benzyl alcohol (3.2 g., 0.03 moles) and triethylamine (3.4 g., 0.03 moles) in dichloromethane (30 ml.). After stirring at 0° for one hour, and at ambient temperature overnight, the mixture is filtered and the filtrate is concentrated in vacuo. The residue (5 g., 90%) becomes semi-solid at room temperature. It is recrystallized from pentane (450 ml.) with a recovery of dimethylphosphinic acid, phenylmethyl ester, yield 3.6 g. (65%) m.p. 41°-45°. A second recrystallization of 0.5 g. from pentane (75 ml.) gives a recovery of 0.26 g. of product, m.p. 46°-47°.

Workup

  1. additionis added dropwise (over a period of 20 minutes),
  2. stirringAfter stirring at 0° for one hour
  3. filtrationat ambient temperature overnight, the mixture is filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customat room temperature
  6. customIt is recrystallized from pentane (450 ml.) with a recovery of dimethylphosphinic acid, phenylmethyl ester, yield 3.6 g
  7. customA second recrystallization of 0.5 g
  8. customfrom pentane (75 ml.) gives a recovery of 0.26 g

Sources & evidence

ORD record
ord-7e09d6f501b44c0d862a69c80b04931d
Source dataset
uspto-grants-1979_09
Patent number
US04168267

Reaction notes

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