Hydrochloric Acid → Ethyl 2-benzylacrylate

HRID 2255775Notes

Reaction equation

HRID 2255775 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 separted, 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. washwashed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-b6040ec4f8a740499614e14493ec54f1
Source dataset
uspto-grants-1993_08
Patent number
US05240924

Reaction notes

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