Ammonium Chloride → 6-Methoxy-1-methoxymethylene-2-(4-methoxyphenyl)-2-methylnaphthalene

HRID 1165514Notes

Reaction equation

HRID 1165514 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH3:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[C:37](=O)[C:36]([C:43]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=1)([CH3:42])[CH2:35][CH2:34]2.[Cl-].[NH4+]>C(OCC)C.CCCCCC>[CH3:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[C:37](=[CH:2][O:3][CH3:4])[C:36]([C:43]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=1)([CH3:42])[CH:35]=[CH:34]2

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 134065446-Methoxy-2-(4-methoxyphenyl)-2-methyltetraloneHCID 178418339Butyllithium

Product 1

HCID 572504956-Methoxy-1-methoxymethylene-2-(4-methoxyphenyl)-2-methylnaphthalene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A suspension of (methoxymethyl)triphenylphosphonium chloride (25.7 g) in diethyl ether (400 ml) was stirred under an argon atmosphere and cooled in an ice-bath while a solution of n-butyl-lithium in hexane (1.6M, 46 ml) was added slowly over 10 minutes. The reaction mixture was then stirred at that temperature for 1 hour. A solution of 6-methoxy-2-(4-methoxyphenyl)-2-methyltetralone (8.9 g ) in diethyl ether 150 ml) was added to the reaction, and it was then stirred at room temperature for 16 h, saturated ammonium chloride solution (300 ml) was added to the reaction mixture and the organic layer was separated. The aqueous layer was extracted twice with diethyl ether (200 ml). The organic extracts were combined, dried and evaporated to dryness. The resulting gum was subjected to flash column chromatography on silica (K60) using toluene as eluting solvent to give 6-methoxy-1-methoxymethylene-2-(4-methoxyphenyl)-2-methylnaphthalene as a colourless oil.

Workup

  1. additionwas added slowly over 10 minutes
  2. stirringThe reaction mixture was then stirred at that temperature for 1 hour
  3. stirringwas then stirred at room temperature for 16 h
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted twice with diethyl ether (200 ml)
  6. customdried
  7. customevaporated to dryness
  8. washas eluting solvent

Sources & evidence

ORD record
ord-51523700d90f4d68b17abc4a78ac7493
Source dataset
uspto-grants-1990_03
Patent number
US04910212

Reaction notes

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