Methyl Ethyl Ketone → HCID 86591060, compound

HRID 1166404Notes

Reaction equation

HRID 1166404 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.C1(C)C(C)=CC=CC=1.[CH3:25][C:26](=[O:29])[CH2:27][CH3:28]>>[CH3:3][OH:2].[O:2]([P:1]([C:26]([OH:29])([CH2:27][CH3:28])[CH3:25])([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]=1

Participants

4

Reactant 3

HCID 6569Methyl Ethyl Ketone2×HCID 7237O-XyleneHCID 23418553Diphenoxyphosphanolate2×

Product 1

HCID 86591060HCID 86591060, compound

Conditions

Temperature
70 °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 xylene were added. The mixture was heated to 70° 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 (72 g) 2-butanone within two hours, and the temperature thereof was increased to 120-1258° C. and maintained at that temperature for six hours after the addition of 2-butanone 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) butan-2-ol methanol [DPOB; (II)]. Yield, 96%; m.p. 52-54° C. Anal. Calcd. for C16H19PO4: C, 62.75; H, 6.21; O, 20.91; P, 10.13. Found: C, 62.61; H, 6.27; O, 20.81; P, 10.31. EIMS, m/z: 306 (92. M+).

Workup

  1. customTo a one liter four-inlet flask equipped with a temperature controller, a reflux condenser
  2. temperatureThe mixture was heated to a temperature of 90° C.
  3. dissolutionwas dissolved completely
  4. temperaturethe temperature thereof was increased to 120-1258° C.
  5. temperaturemaintained at that temperature for six hours
  6. temperatureThe mixture was then cooled to room temperature
  7. customto obtain solid, which
  8. filtrationwas then filtered
  9. custompurified with THF

Sources & evidence

ORD record
ord-88aa1096c69441d8897cb51230b18e68
Source dataset
uspto-grants-2003_09
Patent number
US06613848B1

Reaction notes

Loading…