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

HRID 977906Notes

Reaction equation

HRID 977906 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 gm (0.427 mole) of the ester of Step B in 1500 cc of 1,2-dichloroethane and cool with stirring in an ice-bath. Add 200 cc (345 gm, 1.82 mole) of titanium tetrachloride at a rapid dropwise rate. Add also fairly rapidly 154 gm (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-060f7eefb932451fb0f7b8d8fa83d158
Source dataset
uspto-grants-1987_05
Patent number
US04663307

Reaction notes

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