2-Methoxybenzaldehyde → HCID 54423307, compound

HRID 1383438Notes

Reaction equation

HRID 1383438 reaction equation
C([Li])CCC.[Cl-].[CH3:7][S:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:29][O:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH:33]=O>O1CCCC1>[CH3:29][O:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH:33]=[CH:7][S:8][CH3:9]

Participants

5

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 3083732[(Methylsulfanyl)methyl](triphenyl)phosphanium chlorideHCID 178418339Butyllithium

Product 1

HCID 54423307HCID 54423307, compoundYield 729.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2.6 ml of a 1.6 M butyllithium solution in tetrahydrofuran are slowly added dropwise at 0° C. to a solution of 1.5 g of methylmercaptomethyl-triphenyl-phosphonium chloride in anhydrous tetrahydrofuran. After 1 hour, 5.7 g of 2-methoxybenzaldehyde in 50 ml of tetrahydrofuran are added and the resulting mixture is stirred for a further 12 hours at ambient temperature. The solvent is distilled off in vacuo and the residue remaining is taken up in diethylether. After extraction with dilute, aqueous HCl solution, aqueous Na2CO3 solution (17%) and washing with water, the collected organic phases are dried and the solvent is distilled off in vacuo. Chromatography on silica gel (cyclohexane:ethyl acetate 90:10) yields 5.5 g of 1-methoxy-2-(2-methylsulphanyl-vinyl)-benzene.

Workup

  1. distillationThe solvent is distilled off in vacuo
  2. extractionAfter extraction
  3. additionwith dilute
  4. washaqueous HCl solution, aqueous Na2CO3 solution (17%) and washing with water
  5. customthe collected organic phases are dried
  6. distillationthe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-236008df97d24241b329fa892340c4fc
Source dataset
uspto-grants-2001_07
Patent number
US06255327B1

Reaction notes

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