Potassium Hydroxide → Dimethyl (2-methoxy-phenylsulphanyl)malonate

HRID 37101

Reaction equation

HRID 37101 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[SH:11].Cl[CH:13]([C:18]([O:20][CH3:21])=[O:19])[C:14]([O:16][CH3:17])=[O:15]>C(O)C>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][CH:13]([C:18]([O:20][CH3:21])=[O:19])[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 23642ThioguaiacolHCID 120070Dimethyl chloromalonate

Product 1

HCID 22362038Dimethyl (2-methoxy-phenylsulphanyl)malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1 g of KOH was added to a solution of 2.2 ml of 2-methoxythiophenol in 30 ml of ethanol. The reaction mixture was treated at room temperature with a solution of dimethyl chloromalonate in 5 ml of ethanol, stirred for 1 hour and evaporated. The residue was partitioned between ether and water. The organic phase was dried, concentrated and the residue was purified over silica gel with methylene chloride. 3.6 g of dimethyl (2-methoxy-phenylsulphanyl)malonate, MS: M=270, were obtained.

Workup

  1. customevaporated
  2. customThe residue was partitioned between ether and water
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customthe residue was purified over silica gel with methylene chloride

Sources & evidence

ORD record
ord-19e57d3a32fb454487ce6ca1e155c744
Source dataset
uspto-grants-1995_05
Patent number
US05420129

Linked notes

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