Dimethylamine → 2-Methylene-4-phenylbutyric acid

HRID 1274217Notes

Reaction equation

HRID 1274217 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]([C:13](O)=O)[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CNC.C=O>O>[CH2:13]=[C:9]([CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 1012342-(2-Phenylethyl)malonic acid

Product 1

HCID 138174112-Methylene-4-phenylbutyric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-phenylethylmalonic acid (1.8 g), 40% aqueous dimethylamine (1.08 ml, 1 eq) and 37% aqueous formaldehyde (0.64 ml, 1 eq) in water (10 ml) was stirred at room temperature overnight. After cooling at 0° C. the solid was filtered off, washed with water and dried. The white solid was heated at 170° C. for 10 minutes and cooled to room temperature. The resulting gum was dissolved in ethyl acetate (20 ml), washed with 10% potassium hydrogen sulphate solution (10 ml), water (2×10 ml), saturated brine (10 ml), dried (MgSO4) and evaporated to give crude 2-methylene-4-phenylbutanoic acid. δH (CDCl3) 2.55-2.90 (4H, m, 2×CH2), 5.65, 6.85 (2H, 2×s, H), 7.25 (5H, m, Ph).

Workup

  1. temperatureAfter cooling at 0° C. the solid
  2. filtrationwas filtered off
  3. washwashed with water
  4. customdried
  5. temperatureThe white solid was heated at 170° C. for 10 minutes
  6. temperaturecooled to room temperature
  7. dissolutionThe resulting gum was dissolved in ethyl acetate (20 ml)
  8. washwashed with 10% potassium hydrogen sulphate solution (10 ml), water (2×10 ml), saturated brine (10 ml)
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-0f872f092c36490b9fa192ae84df3a94
Source dataset
uspto-grants-2000_12
Patent number
US06156774

Reaction notes

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