Methane, dichloromethoxy- → 3-(o-Carbomethoxypheylthio-)4-methoxybenzaldehyde

HRID 868326Notes

Reaction equation

HRID 868326 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].[CH3:20][O:21]C(Cl)Cl>ClCCCl.[Ti](Cl)(Cl)(Cl)Cl>[C:12]([C:11]1[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=1[S:9][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH:20]=[O:21])([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 13338684Methyl 2-(o-Methoxyphenylthio)benzoate

Product 1

HCID 133386853-(o-Carbomethoxypheylthio-)4-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Dissolve 117 g (0.427 mole) of the ester of Step B in 1500 ml of 1,2-dichloroethane and cool with stirring in an ice-bath. Add 200 ml (345 g, 1.82 mole) of titanium tetrachloride at a rapid dropwise rate. Add also fairly rapidly 154 g (1.34 mole) of dichloromethyl methyl ether. Stir the mixture under a nitrogen atmosphere overnight then pour into ice. After shaking, separate the organic phase and extract the aqueous phase twice with methylene chloride. Wash the combined organic phases twice with water, dry and strip to an oil which crystallizes. (m.p. 99°-104° C.).

Workup

  1. temperaturecool
  2. stirringStir the mixture under a nitrogen atmosphere overnight
  3. additionthen pour into ice
  4. stirringAfter shaking
  5. customseparate the organic phase
  6. extractionextract the aqueous phase twice with methylene chloride
  7. washWash the combined organic phases twice with water
  8. customdry
  9. customstrip to an oil which crystallizes

Sources & evidence

ORD record
ord-ec411609a2234c22be974cb89d6dee26
Source dataset
uspto-grants-1988_10
Patent number
US04778897

Reaction notes

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