Mesityl oxide → 2-Oxo-2-ethoxy-3,3,5-trimethyl-5-diethylphosphono-1,2-oxaphospholane

HRID 2419169Notes

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].O=[C:17](C=C(C)C)C.[P:23]([O-:30])([O:27]CC)[O:24][CH2:25][CH3:26].[O-]CC.[Na+]>>[O:27]=[P:23]1([O:24][CH2:25][CH3:26])[C:4]([CH3:5])([CH3:17])[CH2:3][C:2]([CH3:7])([P:8]([O:10][CH2:11][CH3:12])([O:13][CH2:14][CH3:15])=[O:9])[O:30]1

Participants

Reactant 4

HCID 8858Mesityl oxide

HCID 2723922Sodium ethoxide2×

HCID 3780918Diethylphosphite2×

HCID 153111314-Methyl-4-diethylphosphonopentan-2-one

Product 1

HCID 544345382-Oxo-2-ethoxy-3,3,5-trimethyl-5-diethylphosphono-1,2-oxaphospholane

Procedure

To a mixture of 2.36 grams (10 m moles) of 4-methyl-4-diethylphosphonopentan-2-one (prepared from 1 mole of mesityl oxide and 1 mole of diethyl phosphite by the procedure of A. N. Pudovik, Zhurn Obshch. Khim., 22, 1371 (1952) and 1.64 grams (11.9 m moles) of diethyl phosphite was added 0.30 gram of ethanolic sodium ethoxide solution containing 0.75 m moles of sodium ethoxide. A spontaneous exothermic reaction took place immediately. After 5 minutes the reaction mixture was analyzed by gas phase chromatography and was shown to contain over 70% of the desired 2-oxo-2-ethoxy-3,3,5-trimethyl-5-diethyl-phosphono-1,2-oxaphospholane. The product was then isolated by vacuum distillation as described in Example 3.

Workup

customA spontaneous exothermic reaction
customThe product was then isolated by vacuum distillation

Sources & evidence

ORD record: ord-8a921a5a08a4497498bc7debdc5ecf63
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04105630

Reaction notes

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