Methoxymethyl-triphenylphosphonium chloride → 2-Phenylnaphthalene

HRID 1514008Notes

Reaction equation

HRID 1514008 reaction equation
[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].C(C1C=C(C2C=CC=CC=2)C=CC=1[C:38]1[CH:47]=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[C:43]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH:44]=2)[CH:39]=1)=O>C1COCC1.C(OCC)C>[C:48]1([C:43]2[CH:44]=[C:45]3[C:40](=[CH:41][CH:42]=2)[CH:39]=[CH:38][CH:47]=[CH:46]3)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

6

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 59434507HCID 59434507, compound

Product 1

HCID 119342-PhenylnaphthaleneYield 83%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In an atmosphere of argon, 823 g (2.40 mol) of (methoxymethyl)triphenylphosphonium chloride and 4 L of dehydrated diethyl ether were charged in a flask. Then, 2.4 L (2.40 mol) of a THF solution of 1M potassium-t-butoxide was added, and the resultant was stirred for 2 hours at room temperature. Then, 6 L of a THF dispersion of 370 g (961 mmol) of 2-(3-formylbiphenyl-4-yl)-6-phenylnapthalene was added dropwise, followed by stirring at room temperature for 17 hours. After the reaction, undissolved matters were filtered, and a filtrate was concentrated. Residues were purified by silica gel chromatography, whereby 330 g of 2-[3-(2-methoxy)ethenyl-1-yl]biphenyl-4-yl]-6-phenylnaphthalene (yield: 83%) was obtained.

Workup

  1. stirringby stirring at room temperature for 17 hours
  2. customAfter the reaction, undissolved matters
  3. filtrationwere filtered
  4. concentrationa filtrate was concentrated

Sources & evidence

ORD record
ord-65c010265ed847a9a0c9a0323190f9b9
Source dataset
uspto-grants-2012_07
Patent number
US08221907B2

Reaction notes

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