Acetic Acid → Dimethyl 2-oxo-3-phenoxypropylphosphonate

HRID 2059034Notes

Reaction equation

C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].[O:13]([CH2:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(=O)C>CCCCCC.O1CCCC1>[O:22]=[C:21]([CH2:20][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyl lithium (69 ml. of a 1.2 M solution in hexane) was added to a solution of dimethyl methylphosphonate (10.3 g.) in dry tetrahydrofuran at -78° C. in an atmosphere of nitrogen. After 10 minutes, a solution of phenoxyacetylchloride (4.1 g.) in dry tetrahydrofuran (20 ml.) was added dropwise, and the mixture was stirred for 4 hours at -78° C. The reaction mixture was neutralised with acetic acid and the solvents were removed under reduced pressure. The residue was shaken with a mixture of ether (100 ml.) and water (20 ml.), and the organic phase was separated and washed with brine. The solution was dried, the solvents were evaporated and the residue was distilled in a bulb distillation apparatus at an oven temperature of 160° C. and 0.1 mm. pressure, to give dimethyl 2-oxo-3-phenoxypropylphosphonate.

Workup

customthe solvents were removed under reduced pressure
stirringThe residue was shaken with a mixture of ether (100 ml.) and water (20 ml.)
customthe organic phase was separated
washwashed with brine
customThe solution was dried
customthe solvents were evaporated
distillationthe residue was distilled in a bulb distillation apparatus at an oven temperature of 160° C. and 0.1 mm

Sources & evidence

ORD record: ord-9ff09d4f83e849d0b2554cd43d0fdff7
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04321275

Reaction notes

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