Hydrochloric Acid → HCID 87574952, compound

HRID 646190Notes

Reaction equation

HRID 646190 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1.[CH3:15][O:16]C(Cl)Cl.Cl>ClCCl.Cl[Ti](Cl)(Cl)Cl>[CH:15]([C:8]1[CH:7]=[C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:4][C:3]=1[O:2][CH3:1])=[O:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 300018Methyl 3-(4-methoxyphenyl)propanoate

Product 1

HCID 87574952HCID 87574952, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

Methyl 3-(4-methoxyphenyl)propanoate (500 mg, 2.56 mmol) was dissolved in 30 mL of anhydrous dichloromethane. TiCl4 (2.1 mL, 19 mmol) and MeOCHCl2 (0.81 mL, 9.0 mmol) were added subsequently at −20° C. under Argon. The reaction mixture was stirred at −20° C. for 6 hours. Then the reaction mixture was slowly poured into a diluted hydrochloric acid solution. The dichloromethane layer was separated and washed with water followed by brine then dried over magnesium sulfate. The solvent was evaporated under reduced pressure. Then the crude residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/10) to obtain methyl 3-(3-formyl-4-methoxyphenyl)propanoate (ss-2) as a colorless oil (429 mg, 75% yield).

Workup

  1. customThe dichloromethane layer was separated
  2. washwashed with water
  3. dry with materialthen dried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThen the crude residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/10)

Sources & evidence

ORD record
ord-4397cda597b94b9db4c732263159cf51
Source dataset
uspto-grants-2010_04
Patent number
US07705040B2

Reaction notes

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