Triphenylphosphine → HCID 20442920, compound

HRID 1632468Notes

Reaction equation

HRID 1632468 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([CH2:11][Cl:12])=[C:6]([CH3:13])[C:5]=1[CH3:14].[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[Cl-:12].[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([CH2:11][P+:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:6]([CH3:13])[C:5]=1[CH3:14]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 13366425HCID 13366425, compound

Product 1

HCID 20442920HCID 20442920, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude (4-trifluoromethoxy-2,3,6-trimethylphenyl)methyl chloride, 27.5 g (0.104 mol) of triphenylphosphine and 250 ml of acetonitrile were heated to reflux for 20 hours. The solvent was removed on a rotary evaporator at room temperature and the residue was triturated with 300 ml of ethyl acetate. The resulting solid was filtered, dissolved in 250 ml of hot acetonitrile and treated with 1 liter of ethyl acetate. The mixture was allowed to stand 2 hours; 38 g of (4-trifluoromethoxy-2,3,6-trimethylphenyl)methyltriphenylphosphonium chloride was collected; mp 272°-274° C. In a similar manner, the mother liquor afforded an additional 10.5 g of product.

Workup

  1. temperatureto reflux for 20 hours
  2. customThe solvent was removed on a rotary evaporator at room temperature
  3. customthe residue was triturated with 300 ml of ethyl acetate
  4. filtrationThe resulting solid was filtered
  5. dissolutiondissolved in 250 ml of hot acetonitrile
  6. additiontreated with 1 liter of ethyl acetate
  7. custom38 g of (4-trifluoromethoxy-2,3,6-trimethylphenyl)methyltriphenylphosphonium chloride was collected

Sources & evidence

ORD record
ord-0a9c9d9bc8964b4594050950d017acd8
Source dataset
uspto-grants-1984_10
Patent number
US04476056

Reaction notes

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