Trimethyl orthoformate → 1-(Dimethoxymethyl)-4-(methylsulfanyl)benzene

HRID 260878Notes

Reaction equation

HRID 260878 reaction equation
[CH:1](OC)([O:4][CH3:5])[O:2][CH3:3].[CH3:8][S:9][C:10]1[CH:17]=[CH:16][C:13](C=O)=[CH:12][CH:11]=1>ClCCl>[CH3:3][O:2][CH:1]([O:4][CH3:5])[C:13]1[CH:16]=[CH:17][C:10]([S:9][CH3:8])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 135965971-(Dimethoxymethyl)-4-(methylsulfanyl)benzeneYield 96.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of K-10 (32 g) in trimethyl orthoformate (115 ml, 1.05 mol) was added to a solution of 4-(methylthio)benzaldehyde (31.0 g, 0.203 mol) in dichloromethane (300 ml) at 0° C. The obtained mixture was stirred at room temperature for 20 minutes and filtered to remove the K-10. The filter cake was washed with dichloromethane. The filtrate and washings were together washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt, dried over magnesium sulfate and concentrated in a vacuum to give the title compound as a pale-yellow oil (39.0 g, 96%).

Workup

  1. filtrationfiltered
  2. customto remove the K-10
  3. washThe filter cake was washed with dichloromethane
  4. washThe filtrate and washings were together washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materiala saturated aqueous solution of common salt, dried over magnesium sulfate
  6. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-76c67a8a4be144a19cbb409218e160df
Source dataset
uspto-grants-1996_06
Patent number
US05530118

Reaction notes

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