2-Propenoic acid, 2-(bromomethyl)-, methyl ester → Methyl 3-methoxy-2-(methoxymethyl)propanoate

HRID 2426961Notes

Reaction equation

HRID 2426961 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][OH:5].Br[CH2:7][C:8](=[CH2:13])[C:9]([O:11][CH3:12])=[O:10]>CO>[CH3:1][O:2][CH2:7][CH:8]([CH2:13][O:5][CH3:4])[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 5210932-Propenoic acid, 2-(bromomethyl)-, methyl esterHCID 23694274Sodium methanolate methanol

Product 1

HCID 22934772Methyl 3-methoxy-2-(methoxymethyl)propanoateYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a 28% sodium methoxide/methanol solution (4.24 g) in methanol (35 mL) was added methyl 2-(bromomethyl)acrylate (1.79 g) in methanol (10 mL). The mixture was stirred at room temperature for 2 hours and was heated to reflux for 3 hours. The reaction mixture was poured into 2N hydrochloric acid-ice, then extracted with ethyl acetate. The obtained organic layer was washed with brine, dried and concentrated to give the title compound (1.33 g) having the following physical data.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe obtained organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-02fbfe27c3224d6db8ec9becf126b0d5
Source dataset
uspto-grants-2011_06
Patent number
US07968572B2

Reaction notes

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