Methacrolein → Ethyl 5-methylsalicylate

HRID 2306130Notes

Reaction equation

HRID 2306130 reaction equation
[CH3:1][C:2](=[CH2:5])[CH:3]=O.Cl[CH:7]([C:13]([CH3:15])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9].C([O-])(=O)C.[Na+]>C(O)(=O)C>[OH:14][C:13]1[CH:15]=[CH:3][C:2]([CH3:5])=[CH:1][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 6562MethacroleinHCID 11858Ethyl 2-chloroacetoacetateHCID 517045Sodium Acetate

Product 1

HCID 118629Ethyl 5-methylsalicylateYield 70.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 2-methylacrolein (22.8 g, 92%, 0.30 mol), ethyl 2-chloroacetoacetate (41.1 g, 95%, 0.25 mol) and anhydrous sodium acetate (24.6 g, 0.30 mol) in acetic acid is heated at reflux temperature under N2 for 16 hr., cooled to room temperature and concentrated in vacuo to give a residue. The residue is partitioned between ethyl acetate and water. The organic phase is concentrated in vacuo to give the title product as an oil, 44.2 g, 71.9% purity (70.6% yield), characterized by NMR analysis).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature under N2 for 16 hr
  3. concentrationconcentrated in vacuo
  4. customto give a residue
  5. customThe residue is partitioned between ethyl acetate and water
  6. concentrationThe organic phase is concentrated in vacuo

Sources & evidence

ORD record
ord-51e8ea498738403ba357dff4865a4ec8
Source dataset
uspto-grants-2002_08
Patent number
US06441219B1

Reaction notes

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