Ethanol → Ethyl 4-chlorocinnamate

HRID 2242563Notes

Reaction equation

HRID 2242563 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5](/[CH:6]=[CH:7]/[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH2:13](O)[CH3:14]>S(=O)(=O)(O)O>[CH2:13]([O:9][C:8](=[O:10])/[CH:7]=[CH:6]/[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:12][CH:11]=1)[CH3:14]

Participants

4

Reactant 2

HCID 702EthanolHCID 6377974-Chlorocinnamic acid

Product 1

HCID 5373977Ethyl 4-chlorocinnamate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
70 °C

Procedure

To a solution of trans-4-chlorocinnamic acid (10 g, 55 mmol) in ethanol (60 mL) was added a catalytic amount of concentrated sulfuric acid (2-3 drops), and the mixture was heated (70° C.) until a majority of the starting material was consumed as evidenced by LCMS. The reaction mixture was concentrated and the contents were redissolved in ethyl acetate. The organic phase was extracted with an aqueous solution of sodium bicarbonate (5%, 3×) followed by a brine wash. The organic phase was dried (MgSO4), filtered and concentrated to afford trans-4-chlorocinnamic acid ethyl ester as a colorless oil. MS (ESI) m/z 211.1 ([M+H]+).

Workup

  1. customwas consumed
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe contents were redissolved in ethyl acetate
  4. extractionThe organic phase was extracted with an aqueous solution of sodium bicarbonate (5%, 3×)
  5. washwash
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5949ce4d83b64e6fb60d0164602020de
Source dataset
uspto-grants-2010_03
Patent number
US07671238B2

Reaction notes

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