Hydrochloric Acid → Ethyl 2-benzylacrylate

HRID 893148Notes

Reaction equation

HRID 893148 reaction equation
[Cl-].[Li+].C(OP([CH:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH2:24]1CCN2C(=NCCC2)CC1.C=O.Cl>C1COCC1.C(OCC)(=O)C.O>[CH2:17]([C:11](=[CH2:24])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27008935085-32-6HCID 433294Lithium Chloride

Product 1

HCID 11084648Ethyl 2-benzylacrylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.0 g of lithium chloride was suspended in 20 ml of THF, and 5 g of ethyl 2-diethylphosphono-3-phenylpropionate was dropwise added thereto. The mixture was stirred at room temperature for seven minutes. Then, 3.6 ml of DBU was added thereto and further 11 minutes later, a suspension of 0.72 g of paraformaldehyde in THF (20 ml) was added thereto at 0° C. The mixture was stirred at room temperature overnight. Then, the mixture was neutralized with 1N hydrochloric acid, and water and ethyl acetate were added thereto. The organic layer was separated, and washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=20/1) to obtain 2.4 g of ethyl 2-benzylacrylate as colorless oily substance.

Workup

  1. additionwas added
  2. customat 0° C
  3. stirringThe mixture was stirred at room temperature overnight
  4. additionwere added
  5. customThe organic layer was separated
  6. washwashed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-fcaff02ef7d646b0868c7fb52702e971
Source dataset
uspto-grants-1992_06
Patent number
US05122523

Reaction notes

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