Acetic Acid → 2-Oxo-2-ethoxy-3,3,5-trimethyl-5-diethylphosphono-1,2-oxaphospholane

HRID 1763804Notes

Reaction equation

C[C:2]([P:8]([O:13][CH2:14][CH3:15])([O:10][CH2:11][CH3:12])=[O:9])([CH3:7])[CH2:3][C:4](=O)[CH3:5].[P:16]([O-:23])([O:20]CC)[O:17][CH2:18][CH3:19].[Na].[C:25](O)(=O)C>C1(C)C=CC=CC=1.[Na]>[O:20]=[P:16]1([O:17][CH2:18][CH3:19])[C:4]([CH3:5])([CH3:25])[CH2:3][C:2]([CH3:7])([P:8]([O:10][CH2:11][CH3:12])([O:13][CH2:14][CH3:15])=[O:9])[O:23]1

Participants

Conditions

Temperature: 80 °C

Procedure

10 ml of a mixture of 70.8 g of 4-methyl-4-(diethylphosphono)-pentan-2-one (prepared from mesityl oxide and diethyl phosphite) and 82.8 g of diethyl phosphite were dissolved in 100 ml of toluene, and the solution was heated to 80° C. A catalytic amount of sodium was added and a vigorous exothermic reaction commenced. The reaction temperature was held between 80° C. and 90° C. by alternately adding the previously prepared mixture and small pieces of sodium. Altogether 1.65 g of sodium was used as catalyst. The reaction took 20 minutes. The reaction mixture was subsequently stirred at 80°-90° C. for 30 minutes with heating, then cooled and neutralized with 4.5 g of glacial acetic acid. This reaction mixture was distilled to yield 2-oxo-2-ethoxy-3,3,5-trimethyl-5-diethylphosphono-1,2-oxaphospholane with a boiling point of 156°-161° C./1.1 mm. This substance is identical to the oxaphospholane manufactured according to Example 4.

Workup

customa vigorous exothermic reaction
customwas held between 80° C. and 90° C.
temperaturewith heating
temperaturecooled
distillationThis reaction mixture was distilled

Sources & evidence

ORD record: ord-a3401e9115944a33b79341aaeda3b5c0
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04113669

Reaction notes

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