Dichloromethane → HCID 88225702, compound

HRID 1386477Notes

Reaction equation

HRID 1386477 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9]([CH3:15])([CH3:14])[CH2:8][CH2:7][C:6]2([CH3:17])[CH3:16].[C:18]1([P:24]([C:31]2C=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl[CH2:38]Cl>C(OCC)C>[Br-:1].[CH3:13][C:12]1[C:3]([C:2]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[P+:24]([CH3:38])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:4][C:5]2[C:6]([CH3:17])([CH3:16])[CH2:7][CH2:8][C:9]([CH3:15])([CH3:14])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 21717666HCID 21717666, compound

Product 1

HCID 88225702HCID 88225702, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The raw 6-bromomethyl-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (8.80 g, about 32 mmol) prepared previously is mixed with triphenylphosphine (10.1 g, 38.4 mmol) in solution in 50 ml of dichloromethane for 24 hours, then diluted with ethyl ether (200 ml). The [(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-methyl]triphenylphosphonium bromide precipitates, is filtered and washed abundantly with the ether. 10.72 g of white crystals (5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-methyl-triphenylphosphonium bromide is obtained after drying (yield=60%).

Workup

  1. customThe [(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-methyl]triphenylphosphonium bromide precipitates
  2. filtrationis filtered
  3. washwashed abundantly with the ether

Sources & evidence

ORD record
ord-0f53f358cbd04c4cb98aa4d90cba2482
Source dataset
uspto-grants-2001_07
Patent number
US06265423B1

Reaction notes

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