Veratraldehyde → 2-[(3,4-Dimethoxyphenyl)methylidene]-1,3-dithiolane

HRID 1708999Notes

Reaction equation

HRID 1708999 reaction equation
C(OP([CH:9]1[S:14][CH2:13][CH2:12]C[S:10]1)(OCC)=O)C.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:20]=O.[OH-].[Na+]>ClCCl.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[S:14]1[CH2:13][CH2:12][S:10][C:9]1=[CH:20][C:19]1[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:17]([O:16][CH3:15])[CH:18]=1

Participants

6

Reactant 3

HCID 8419VeratraldehydeHCID 14798Sodium HydroxideHCID 10869064Diethyl (1,3-Dithian-2-yl)phosphonate

Product 1

HCID 230390002-[(3,4-Dimethoxyphenyl)methylidene]-1,3-dithiolane

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-diethoxyphosphoryl-1,3-dithiane (23.4 g) and 3,4-dimethoxybenzaldehyde (16.0 g) in dichloromethane (70 ml) is added to a mixture of dichloromethane (85 ml), a 50% aqueous solution of sodium hydroxide (170 ml) and triethylbenzylammonium chloride (1.4 g). The mixture is stirred for 24 hours at room temperature. The two phases are then separated. The aqueous solution is extracted with dichloromethane (100 ml) and the combined organic solutions are washed with a 10% aqueous solution of ammonium chloride (3×100 ml) and with water (2×100 ml). The dichloromethane is dried over magnesium sulphate and evaporated in vacuo. The residue is purified by column chromatography on silica gel using chloroform as eluant. The product is dried in vacuo to constant weight to yield (1,3-dithiolan-2-ylidene)-(3,4-dimethoxyphenyl)methane, m.p. 74°--75°.

Workup

  1. customThe two phases are then separated
  2. extractionThe aqueous solution is extracted with dichloromethane (100 ml)
  3. washthe combined organic solutions are washed with a 10% aqueous solution of ammonium chloride (3×100 ml) and with water (2×100 ml)
  4. dry with materialThe dichloromethane is dried over magnesium sulphate
  5. customevaporated in vacuo
  6. customThe residue is purified by column chromatography on silica gel
  7. customThe product is dried in vacuo to constant weight

Sources & evidence

ORD record
ord-1132c83717f5411887c79b4eced7503e
Source dataset
uspto-grants-1990_08
Patent number
US04946861

Reaction notes

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