Triphenylphosphine → (6-Cyano-1,2,3,4-tetrahydro-2-naphthyl)methyltriphenylphosphonium p-toluenesulfonate

HRID 1738669Notes

Reaction equation

HRID 1738669 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[CH:18]=[C:17]([C:22]#[N:23])[CH:16]=[CH:15][C:14]=3[CH2:13]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:25]1([P:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[C:1]1([CH3:24])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[C:22]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH:12]([CH2:11][P+:31]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:21][CH2:20]2)#[N:23]

Participants

3

Reactant 2

HCID 11776TriphenylphosphineHCID 134887305,6,7,8-Tetrahydro-6-[(p-toluenesulfonyl)oxymethyl]-2-naphthalenecarbonitrile

Product 1

HCID 21844271(6-Cyano-1,2,3,4-tetrahydro-2-naphthyl)methyltriphenylphosphonium p-toluenesulfonateYield 55.1%

Conditions

Temperature
135 °C

Procedure

24.00 g of 5,6,7,8-tetrahydro-6-[(p-toluenesulfonyl)oxymethyl]-2-naphthalenecarbonitrile and 18.38 g of triphenylphosphine were mixed, and then heated at a temperature of 130 to 140° C. for 15 hours in a sealed container. The resulting reaction product was crystallized from an acetone/n-hexane mixture to obtain 23.3 g of the title compound in the form of light yellow powder.

Workup

  1. customThe resulting reaction product
  2. customwas crystallized from an acetone/n-hexane mixture

Sources & evidence

ORD record
ord-bca015bab2564a5c86e9833c49467c55
Source dataset
uspto-grants-1999_10
Patent number
US05962695

Reaction notes

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