1-Butanol → Butyl 3-phenylprop-2-enoate

HRID 18911Notes

Reaction equation

HRID 18911 reaction equation
[CH:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([C:13]1C(=O)C(Cl)=C(Cl)[C:15](=[O:16])[C:14]=1C#N)#N.C(O)CCC.O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>C1(C)C=CC=CC=1>[C:1]([O:16][CH2:15][CH2:14][CH2:13][CH3:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 3073-Phenylprop-2-EnalHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 71586775Bentonite

Product 1

HCID 10861Butyl 3-phenylprop-2-enoateYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A homogeneous mixture containing cinnamaldehyde (7.5 mmol), DDQ (11.3 mmol), BuOH (10 mL) and toluene (15 mL) is taken in a round bottom flask and catalytic amount of AMBERLYST® 15 (0.1 g) is added to it. The mixture is refluxed for 6 hrs under Dean Stark apparatus. After completion of the reaction (observed by TLC and by GC analysis), the reaction mixture is filtered and washed with ethylacetate (5 ml×2). Concentrate the filtrate under reduced pressure and the crude product thus obtained is loaded on a neutral alumina column and eluted with diethyl ether. Butyl cinnamate (from formula I where X1═H, X2═H, X3═H, X4═H, X5═H, R═C4H9) is isolated in 94% yield. 1H-NMR (CDCl3, 300 MHz) δ7.48 (1H, d), 7.25 (2H, m), 7.11 (3H, m), 6.23 (1H, m), 3.98 (2H, t), 1.45 (2H, m), 1.19 (2H, m), 0.74 (3H, t); 13C-NMR (CDCl3, 75.4 MHz) δ166.5, 144.2, 134.4, 129.9, 127.9, 118.2, 64.0, 30.7, 19.1, 13.6.

Workup

  1. customis taken in a round bottom flask
  2. temperatureThe mixture is refluxed for 6 hrs under Dean Stark apparatus
  3. customAfter completion of the reaction (observed by TLC and by GC analysis)
  4. filtrationthe reaction mixture is filtered
  5. washwashed with ethylacetate (5 ml×2)
  6. concentrationConcentrate the filtrate under reduced pressure
  7. customthe crude product thus obtained
  8. washeluted with diethyl ether

Sources & evidence

ORD record
ord-540cb1eae3d04860861ade46f9648f87
Source dataset
uspto-grants-2010_06
Patent number
US07741508B2

Reaction notes

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