4-Methylanisole → Ethyl 4-(2-methoxy-5-methylphenyl)-4-oxobutanoate

HRID 2290926Notes

Reaction equation

HRID 2290926 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]([CH2:15][CH2:16][C:17](Cl)=[O:18])([O:12][CH2:13][CH3:14])=[O:11].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH2:13]([O:12][C:10](=[O:11])[CH2:15][CH2:16][C:17](=[O:18])[C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[CH3:14]

Participants

5

Reactant 3

HCID 77314-MethylanisoleHCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20230698Ethyl 4-(2-methoxy-5-methylphenyl)-4-oxobutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of p-methylanisole (100 g, 0.81 mole), β-carbethoxypropionylchloride (96%, 230 g, 1.22 mole), and CH2Cl2 (800 mL) was stirred under N2 at 0° as AlCl3 (131 g, 0.94 mole) was added over 2 hours. The reaction mixture was stirred at room temperature for 20 hours, then was poured onto ice and the layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with water, saturated aqueous NaHCO3, 1N KOH, H2O, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated (in-vacuo) to obtain a yellow oil.

Workup

  1. additionwas added over 2 hours
  2. additionwas poured onto ice
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. washThe combined organic layers were washed with water, saturated aqueous NaHCO3, 1N KOH, H2O, saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated (in-vacuo)
  9. customto obtain a yellow oil

Sources & evidence

ORD record
ord-89284b5b032b40b1991ec2f9b8c4e2cd
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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