2-Methylnaphthalene → Benzyldiphenylphosphine

HRID 260581Notes

Reaction equation

HRID 260581 reaction equation
[Cl-].[Mg+2].[Cl-].Cl[P:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=CC=CC=2)[CH:20]=1>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C)C=O>[CH2:18]([P:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:19]1[CH:28]=[CH:27][CH:26]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 70552-MethylnaphthaleneHCID 66180ChlorodiphenylphosphineHCID 5360315Magnesium Chloride

Product 1

HCID 603920BenzyldiphenylphosphineYield 83%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

An electrolysis cell as described in Example 1 is used. The electrolyte comprises 70 ml of dimethylformamide (max. 0.1% of water), 0.4 g of anhydrous magnesium chloride and 6.62 g (0.030 mol) of chlorodiphenylphosphine. The electrolysis is carried out as described in Example 1. The electrolysis temperature is 25° C. After an amount of charge of 0.96 Ah, the electrolysis is ended. 4.64 g (0.025 mol) of benzyltrimethylammonium chloride are then introduced into the electrolyte with exclusion of air and the mixture is stirred at 35° C. After 3 h the reaction mixture contains, according to analysis by gas chromatography (internal standard: 2-methylnaphthalene), 5.72 g of benzyldiphenylphosphine (yield 83%, based on benzyltrimethylammonium chloride used) which can be isolated by workup as described in Example 1.

Workup

  1. customis 25° C
  2. additionAfter an amount of charge of 0.96 Ah

Sources & evidence

ORD record
ord-9eb794d000ea4aeabd7c743863d0fa16
Source dataset
uspto-grants-1996_06
Patent number
US05527967

Reaction notes

Loading…