Benzaldehyde → Ethyl Cinnamate

HRID 475056

Reaction equation

HRID 475056 reaction equation
CC(C)([O-])C.[Li+].C(OP([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(OCC)=O)C.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[C:22]1(/[CH:21]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 13345Triethyl phosphonoacetateHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

Product 1

HCID 637758Ethyl CinnamateYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred mixture of lithium tert-butoxide (124.6 g, 1.56 mol, 1.10 equiv) in DCM (2000 mL) under N2 at RT was added ethyl 2-(diethoxyphosphoryl)acetate (317 g, 1.41 mol, 1.00 equiv). Benzaldehyde (150 g, 1.41 mol, 1.0 equiv) was then added dropwise to the stirred reaction, and the resulting reaction mixture was stirred under N2 at 25° C. overnight. The reaction mixture was diluted with DCM (2 L). The organic layer was washed with water (3×2 L) and brine (1×2 L), dried (Na2SO4), filtered, and evaporated in vacuo. The crude residue was purified by SiO2 chromatograph eluting with EtOAc/petroleum ether (3.3 to 1% EtOAc) to afford 180 g (72%) of ethyl (2E)-3-phenylprop-2-enoate (31) as a light yellow oil.

Workup

  1. customthe resulting reaction mixture
  2. washThe organic layer was washed with water (3×2 L) and brine (1×2 L)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude residue was purified by SiO2 chromatograph
  7. washeluting with EtOAc/petroleum ether (3.3 to 1% EtOAc)

Sources & evidence

ORD record
ord-2a24aa8a602940fea7000c23a6bea6f5
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Linked notes

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