Thionyl Chloride → Methyl 2-[3-(phenylchloromethyl)phenyl]propionate

HRID 1590695Notes

Reaction equation

HRID 1590695 reaction equation
[C:1]1([CH:7](O)[C:8]2[CH:9]=[C:10]([CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:23])=O>C(Cl)Cl>[C:1]1([CH:7]([Cl:23])[C:8]2[CH:9]=[C:10]([CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10492268Methyl 2-[3-(phenylhydroxymethyl)phenyl]propionate

Product 1

HCID 10613388Methyl 2-[3-(phenylchloromethyl)phenyl]propionateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 2-[3-(phenylhydroximethyl)phenyl]propionate (128 g) was dissolved in 100 mL of dry methylene chloride and the solution was cooled to 0° C. Then 41 mL of thionyl chloride in 50 mL methylene chloride were added along 1 hour, keeping the reaction temperature between 5 and 10° C. After staying for 1 hour at 5° C. and 1 hour at room temperature, solvents were removed and the residue (130.5 g, yellow oil) was vacuum distilled, yielding 103 g (75% yield) of the title compound as a yellow transparent liquid, b.p. 158-163° C./1 tor. In the 200 MHz 1H-NMR apparatus the signal of CH3 -- appears as two doublets of similar intensity, indicating the presence of the two possible diasteromers. By following analogous procedures, compounds IIc of Table 3 were obtained.

Workup

  1. customthe reaction temperature between 5 and 10° C
  2. customsolvents were removed
  3. distillationdistilled

Sources & evidence

ORD record
ord-5e18520a6dc14b658566215b0aadd354
Source dataset
uspto-grants-1993_04
Patent number
US05204365

Reaction notes

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