Methoxymethyl-triphenylphosphonium chloride → HCID 19601703, compound

HRID 2397298Notes

Reaction equation

HRID 2397298 reaction equation
[Cl-].[CH3:2][O:3]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1([Li])C=CC=CC=1.[CH3:31][CH:32]([CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[CH:33]=O>CCOCC>[CH3:31][CH:32]([CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:33][CH:2]=[O:3]

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 19349187HCID 19349187, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 19601703HCID 19601703, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of 21 grams of methoxymethyltriphenylphosphonium chloride in 200 ml. of absolute ether is added under nitrogen at room temperature a solution of 60 mmoles of phenyllithium in ether. After about 10 minutes, the mixture is cooled to -30° and 6 grams of 2,5-dimethylhexan-1-al in ether is added slowly. After about 12 hours at room temperature, the mixture is filtered and the filtrate evaporated. The concentrate is dissolved in aqueous tetrahydrofuran containing a small amount of dilute hydrochloric acid and stirred at room temperature for about 48 hours. The mixture is worked up in ether to yield 3,6-dimethylheptan-1-al which is purified by chromatography.

Workup

  1. temperaturethe mixture is cooled to -30°
  2. waitAfter about 12 hours at room temperature
  3. filtrationthe mixture is filtered
  4. customthe filtrate evaporated
  5. dissolutionThe concentrate is dissolved in aqueous tetrahydrofuran containing a small amount of dilute hydrochloric acid

Sources & evidence

ORD record
ord-fa85999f122e405db7e7953a3f14d4b5
Source dataset
uspto-grants-1977_05
Patent number
US04021461

Reaction notes

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