Ethanol → HCID 12596498, compound

HRID 1421881Notes

Reaction equation

HRID 1421881 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].[CH2:11]([O:13]C(OCC)OCC)[CH3:12].[CH2:21](O)[CH3:22]>>[CH2:21]([O:4][C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([O:13][CH2:11][CH3:12])[CH2:2][CH3:3])[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 71481-Phenyl-1-propanoneHCID 31214Ethyl orthoformate

Product 1

HCID 12596498HCID 12596498, compoundYield 71%

Procedure

To a solution of propiophenone (20 mL, 0.15 mol) in ethanol (EtOH) (20 mL) was added triethylorthoformate (32.4 mL, 0.20 mol). A stream of HCl gas was bubbled through this solution for approximately 15 seconds, then the golden solution was stirred for 20 hours at ambient temperature. The solution was then treated with NaOMe/EtOH until basic, followed by filtration. The filtrate was concentrated by removal of the EtOH in vacuo. The product was isolated via vacuum distillation to give the title compound (22.2 g, 71%). 1H NMR (300 MHz, CDCl3)δ7.51-7.47 (m, 2H), δ7.36-7.23 (m, 3H), δ3.47-3.17 (m, 4H), δ1.92 (quartet, J=7.5 Hz, 2H), δ1.20 (t, J=7.1 Hz, 6H), δ0.57 J=7.5 Hz, 3H).

Workup

  1. customA stream of HCl gas was bubbled through this solution for approximately 15 seconds
  2. additionThe solution was then treated with NaOMe/EtOH until basic,
  3. filtrationfollowed by filtration
  4. concentrationThe filtrate was concentrated by removal of the EtOH in vacuo
  5. customThe product was isolated via vacuum distillation

Sources & evidence

ORD record
ord-94ff63e7ad154d0591fc51842a70fba7
Source dataset
uspto-grants-2000_06
Patent number
US06080757

Reaction notes

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