Acetone → 2-(Diphenoxy phosphoryl) propan-2-ol
Reaction equation
[P:1]([O-:16])([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1COCC1.[CH3:22][C:23]([CH3:25])=[O:24]>>[O:2]([P:1]([C:23]([OH:24])([CH3:25])[CH3:22])([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1Participants
Conditions
- Temperature
- 50 °C
Procedure
To a one liter four-inlet flask equipped with a temperature controller, a reflux condenser, a nitrogen feed and a mechanical stirrer, 1 mole (234 g) diphenyl phosphite (DPP) and 500 ml THF were added. The mixture was heated to 50° C. and then stirred. The mixture was heated to a temperature of 90° C. and the stirring was continued until DPP was dissolved completely. To this solution was added slowly 1.0 mole (58 g) acetone within two hours, and the temperature thereof was increased to 70° C. and maintained at that temperature for four hours after the addition of acetone was completed. The mixture was then cooled to room temperature to obtain solid, which was then filtered, and purified with THF to yield 2-(diphenoxy phosphoryl) propan-2-ol [DPOP; (II)]. Yield, 96%; m.p. 70–72° C. Anal. Calcd. for C15H17PO4: C, 61.64; H, 5.82; O, 21.92; P, 10.62. Found: C, 61.52; H, 5.96; O, 21.78; P, 10.74. EIMS, m/z: 292 (92. M+).
Workup
- customTo a one liter four-inlet flask equipped with a temperature controller, a reflux condenser
- temperatureThe mixture was heated to a temperature of 90° C.
- dissolutionwas dissolved completely
- temperaturethe temperature thereof was increased to 70° C.
- temperaturemaintained at that temperature for four hours
- temperatureThe mixture was then cooled to room temperature
- customto obtain solid, which
- filtrationwas then filtered
- custompurified with THF
Sources & evidence
- ORD record
- ord-6f048f8e98a2462faf3f5a9e009db66d
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06992151B2
Reaction notes
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