Triphenylphosphine → HCID 11353265, compound

HRID 1386482Notes

Reaction equation

HRID 1386482 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]2([CH3:16])[CH3:15].[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>ClCCl.C(OCC)C>[Br-:1].[CH3:13][C:9]1([CH3:14])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]2[CH:4]=[C:3]([CH2:2][P+:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:12]=[CH:11][C:10]1=2

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 27355976-(Bromomethyl)-1,1,4,4-Tetramethyl-1,2,3,4-Tetrahydronaphthalene

Product 1

HCID 11353265HCID 11353265, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

The 6-bromomethyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (9.0 g, 32.0 mmol) prepared in the previous step is mixed with triphenylphosphine (10.1 g, 38.4 mmol) in solution in 50 ml of dichloromethane for 24 hours, and then diluted with ethyl ether (200 ml). The (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)methyl-triphenyl-phosphonium bromide precipitates, is filtered and washed with ether. The white crystals obtained (15.0 g, yield 86%) are dried in a desiccator.

Workup

  1. customThe (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)methyl-triphenyl-phosphonium bromide precipitates
  2. filtrationis filtered
  3. washwashed with ether
  4. customThe white crystals obtained (15.0 g, yield 86%)
  5. customare dried in a desiccator

Sources & evidence

ORD record
ord-c00f809a42054b24812b119a0002cc61
Source dataset
uspto-grants-2001_07
Patent number
US06265423B1

Reaction notes

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