Ethanol → Ethyl methoxycinnamate

HRID 1774264Notes

Reaction equation

HRID 1774264 reaction equation
[Si](OI)(C)(C)C.[H-].[Na+].[CH3:9][O:10][C:11]1[CH:21]=[CH:20][C:14](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:13][CH:12]=1.OS(O)(=O)=O.[CH3:27][CH2:28]O>CS(C)=O>[CH3:9][O:10][C:11]1[CH:21]=[CH:20][C:14](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:27][CH3:28])=[O:18])=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 1118Sulfuric AcidHCID 24758Sodium hydrideHCID 6994144-Methoxycinnamic AcidHCID 90346114HCID 90346114, compound

Product 1

HCID 5281783Ethyl methoxycinnamateYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

Compounds 100, 105, 107, and 106 were synthesized under the Corey-Chaykovsky cyclopropanation reaction conditions (TMSOI, NaH, DMSO). A mixture of trans-4-methoxycinnamic acid (18 g, 101 mmol) and concentrated H2SO4 (0.5 mL) in absolute EtOH (100 mL) was refluxed at 90° C. (bath temperature) for 16 h. After the excess EtOH was removed by a rotary evaporator, the residue was treated with H2O (100 mL), and the resulting mixture was extracted with ether (3×120 mL). The combined extracts were washed with 1N aq. NaOH (2×50 mL), H2O (80 mL) and brine (80 mL), and dried (anhydrous Na2SO4). The solvent was evaporated to dryness to give ethyl trans-4-methoxycinnamate (20 g, 96% yield) as light yellow oil.

Workup

  1. customAfter the excess EtOH was removed by a rotary evaporator
  2. additionthe residue was treated with H2O (100 mL)
  3. extractionthe resulting mixture was extracted with ether (3×120 mL)
  4. washThe combined extracts were washed with 1N aq. NaOH (2×50 mL), H2O (80 mL) and brine (80 mL)
  5. dry with materialdried (anhydrous Na2SO4)
  6. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-d92398b7d020470bb46517f5847e8e93
Source dataset
uspto-grants-2016_02
Patent number
US09260382B2

Reaction notes

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