4-Chlorobenzaldehyde → Diethyl P-((4-chlorophenyl)hydroxymethyl)phosphonate

HRID 1460992Notes

Reaction equation

HRID 1460992 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[P:10]([O-:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[OH:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 3780918Diethylphosphite

Product 1

HCID 89363Diethyl P-((4-chlorophenyl)hydroxymethyl)phosphonateYield 99.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere a solution of 20.0 grams (0.143 mole) of 4-chlorobenzaldehyde and 19.7 grams (0.142 mole) of diethyl phosphite was stirred at ambient temperature for 4 days. Gas chromatographic analysis of the reaction mixture indicated the reaction had not gone to completion. Ten ml of triethylamine was added, and the reaction mixture was stirred at ambient temperature for an additional 4 days. Gas chromatographic analysis of the reaction mixture indicated the reaction mixture still had not gone to completion. The reaction mixture was warmed to 40°-50° C. where it was stirred for 24 hours. After this time the reaction mixture was concentrated under reduced pressure, yielding 39.2 grams of diethyl (4-chlorophenyl)hydroxymethylphosphonate.

Workup

  1. temperatureThe reaction mixture was warmed to 40°-50° C. where it
  2. stirringwas stirred for 24 hours
  3. concentrationAfter this time the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b056500e66a74f749934260fb037bea6
Source dataset
uspto-grants-1991_12
Patent number
US05073564

Reaction notes

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