Methanol → HCID 21453530, compound

HRID 436247Notes

Reaction equation

HRID 436247 reaction equation
O=P(Cl)(Cl)Cl.[Cl:6][CH:7]([CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])[CH2:8][OH:9].N1C=CC=CC=1.[CH3:21]O.[P:23]([O-:37])([O-:36])([O:25][C:26](C)(C)C(Cl)CC(Cl)(Cl)Cl)=O.P([O-])([O-])([O-])=O>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[P:23]([O:9][CH2:8][CH:7]([Cl:6])[CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])([O:25][CH3:26])([O:37][CH3:21])=[O:36]

Participants

9

Reactant 6

HCID 887MethanolHCID 1049Pyridine2×HCID 1061PhosphateHCID 186882,4,4,4-Tetrachlorobutan-1-olHCID 24813Phosphorus oxychlorideHCID 86734493HCID 86734493, compound

Product 1

HCID 21453530HCID 21453530, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

Into a 3-necked flask fitted with a stirrer, thermometer and drying tube, a solution of 91.8 g. (0.6 mole) POCl3 and 127 g. (0.6 mole) 2,4,4,4-tetrachlorobutanol in a mixture of 400 mls. of carbon tetrachloride and 100 mls. of chloroform was poured. A total of 52 g. (0.67 mole) of pyridine was added dropwise while stirring and holding the temperature below 12° C. A mixture of 42 g. (1.3 moles) of methanol in 104 g. (1.3 moles) of pyridine was added while keeping the temperature below 21° C. After completion of the reaction the organic phase was successively washed with aqueous 20% H2SO4 solution, water, saturated aqueous NaHCO3, and water. The solution was dried and concentrated at reduced pressure to give 158 g. (82%) of dimethyl-2,4,4,4-tetrachlorobutyl phosphate. Distillation at 130° C./0.3 mm. gave a purified product having n(24/D) 1.4766. The phosphate structure was substantiated by infrared analysis. Elemental Analysis: Calcd. for C6H11Cl4O4P: percent Cl, 44.38; percent P, 9.69 Found: percent Cl, 45.49; percent P, 9.48.

Workup

  1. customInto a 3-necked flask fitted with a stirrer
  2. customthermometer and drying tube
  3. customthe temperature below 12° C
  4. additionA mixture of 42 g
  5. customthe temperature below 21° C
  6. customAfter completion of the reaction the organic phase
  7. washwas successively washed with aqueous 20% H2SO4 solution, water, saturated aqueous NaHCO3, and water
  8. customThe solution was dried
  9. concentrationconcentrated at reduced pressure
  10. customto give 158 g
  11. distillationDistillation at 130° C./0.3 mm
  12. customgave a purified product

Sources & evidence

ORD record
ord-51f7eb8d34cd4cba89cf711cca32a19e
Source dataset
uspto-grants-1977_02
Patent number
US04008187

Reaction notes

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