Diethyl [(4-benzoylphenyl)methyl]phosphonate → Phosphonic acid, [(4-benzoylphenyl)methyl]-

HRID 1728442Notes

Reaction equation

HRID 1728442 reaction equation
C([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(=[O:8])[O:5]CC)C>Cl>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:9][P:4](=[O:3])([OH:5])[OH:8])=[CH:11][CH:12]=1)(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 1

HCID 56986843Diethyl [(4-benzoylphenyl)methyl]phosphonate

Product 1

HCID 9795572Phosphonic acid, [(4-benzoylphenyl)methyl]-Yield 26.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4.8 g of 4-benzoylbenzyl bromide and triethylphosphite was heated at 125° C. for 0.5 hours and cooled to room temperature. The resulting oil was purified by flash chromatography (70% ethyl acetate/hexanes) to afford 3.2 g of diethyl 4-benzoylbenzylphosphonic acid, as an oil. A mixture of 3.2 g (9.6 mmol) of diethyl 4-benzoylbenzylphosphonic acid and 40 ml of concentrated hydrochloric acid was refluxed for 7 hours and cooled to room temperature. The two phase mixture was partitioned between 125 ml of water and 400 ml of EtOAc, the EtOAc layer was dried over Na2SO4, filtered and evaporated to give 0.7 g of product; m.p. 172°-175° C.

Workup

  1. temperaturewas refluxed for 7 hours
  2. customThe two phase mixture was partitioned between 125 ml of water and 400 ml of EtOAc
  3. dry with materialthe EtOAc layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ee65471b454c41c88d762da6dd8843fa
Source dataset
uspto-grants-1994_07
Patent number
US05326905

Reaction notes

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