Acetic Acid → 4-methoxybenzyltriphenylphosphonium Acetate acetic Acid

HRID 1033271Notes

Reaction equation

HRID 1033271 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][P+:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[C:30]([OH:33])(=[O:32])[CH3:31].N>C1C=CC=CC=1>[C:30]([O-:33])(=[O:32])[CH3:31].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][P+:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:28][CH:29]=1.[C:30]([OH:33])(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 222AmmoniaHCID 2773651(4-Methoxybenzyl)triphenylphosphonium chloride

Product 1

HCID 189582264-methoxybenzyltriphenylphosphonium Acetate acetic AcidYield 72.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
40 °C

Procedure

Into a 50 milliliter glass reactor equipped with a thermometer connected to a temperature controller, a heating mantle, a condenser and a magnetic stirring bar, is charged 9 gms (0.0215 mole) of 4-methoxybenzyl triphenyl phosphonium chloride and 25 gms of acetic acid. The mixture is heated to 40° C. then 1 gm (0.0588 mole) of ammonia is added. This reaction mass is heated to 80° C. and maintained there for 1.17 hours, then heated to 100° C. and maintained thereat for 18 hours, then heated to 110° C. and maintained thereat 4.8 hours, and then cooled to 30° C. To this is added 40 g of benzene and the contents let stand overnight to settle the solids, then the liquid is removed by decantation and vacuum distillation to obtain 7.8 g of product having a melting point of 121° C. to 130° C.

Workup

  1. customInto a 50 milliliter glass reactor equipped with a thermometer
  2. temperatureThis reaction mass is heated to 80° C.
  3. temperaturemaintained there for 1.17 hours
  4. temperatureheated to 100° C.
  5. temperaturemaintained
  6. temperatureheated to 110° C.
  7. temperaturemaintained
  8. temperature4.8 hours, and then cooled to 30° C
  9. waitthe contents let stand overnight
  10. customthe liquid is removed by decantation and vacuum distillation

Sources & evidence

ORD record
ord-28600fceedf74844b4b003553b5bb6c7
Source dataset
uspto-grants-1994_05
Patent number
US05310853

Reaction notes

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