Hydrochloric Acid → 2-Benzylacrylic Acid

HRID 8306

Reaction equation

HRID 8306 reaction equation
[CH2:1]([CH:8]([C:12](O)=O)[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.C(NCC)C.Cl>C(OCC)(=O)C.O>[CH2:12]=[C:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([OH:11])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8021DiethylamineHCID 12031Benzylmalonic acid

Product 1

HCID 3035712-Benzylacrylic AcidYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzylmalonic acid (20.0 g, 0.103 mol, 1 eq) and paraformaldehyde (4.94 g, 0.164 mol, 1.6 eq) in ethyl acetate (150 mL) was cooled (0° C.) and treated with diethylamine (10.65 mL, 0.103 mol, 1 eq) drop wise, keeping the reaction temperature below 20° C. The reaction was then warmed to reflux for 90 minutes and cooled again on ice. The homogeneous solution was treated with water (20 mL) and concentrated aqueous HCl (12N) (9.0 mL, 0.108 mol) drop wise, keeping the reaction temperature below 10° C. The phases were then separated. The organic layer was washed with brine (100 mL), dried over sodium sulfate, filtered, and the filtrate concentrated under vacuum giving 2-methylene-3-phenylpropanoic acid (10) as a white solid (15 g, 90%).

Workup

  1. customthe reaction temperature below 20° C
  2. temperatureThe reaction was then warmed
  3. temperatureto reflux for 90 minutes
  4. temperaturecooled again on ice
  5. customthe reaction temperature below 10° C
  6. customThe phases were then separated
  7. washThe organic layer was washed with brine (100 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-955486293bfd46269894a00172777c35
Source dataset
uspto-grants-2006_08
Patent number
US07087749B2

Linked notes

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