Perchloric Acid → HCID 12927152, compound

HRID 1856430Notes

Reaction equation

HRID 1856430 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][P:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:12])O.Cl(O)(=O)(=O)=O>C(OCC)C>[C:13]1([P:10]2(=[O:12])[C:8]3[CH:7]=[CH:6][CH:5]=[CH:2][C:3]=3[CH2:4][O:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 86737159HCID 86737159, compound

Product 1

HCID 12927152HCID 12927152, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
26 °C

Procedure

A mixture of 2-bromomethylphenyl-phenylphosphonic acid (3.95 g, 0.0127 mole) and 10 ml. of 10% perchloric acid was heated at 100° C. for 4.5 hours with constant stirring. The reaction mixture was cooled to 26° C. and then extracted with methylene chloride. The methylene chloride layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to yield a yellow oil. This oil was distilled in a Kugelrohr at 180° C. and 0.6 torr to yield a colorless oil. The colorless oil was slurried in anhydrous diethyl ether, cooled during which period crystallization occured and then filtered to yield 1-phenyl-1,3-dihydro-2,1-benzoxaphosphole-1-oxide (2.2 g, 76% yield) as white crystals having a melting point of 99°-101° C. and the following analysis:

Workup

  1. extractionextracted with methylene chloride
  2. washThe methylene chloride layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto yield a yellow oil
  6. distillationThis oil was distilled in a Kugelrohr at 180° C.
  7. custom0.6 torr to yield a colorless oil
  8. temperaturecooled during which period crystallization
  9. filtrationfiltered

Sources & evidence

ORD record
ord-2bc8e3f3971e43ef99d5f5ce139123a1
Source dataset
uspto-grants-1980_08
Patent number
US04219510

Reaction notes

Loading…