Ethanol → HCID 22906421, compound

HRID 1379811Notes

Reaction equation

HRID 1379811 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.C(OCC)(OCC)[O:13][CH2:14][CH3:15].[CH3:22][CH2:23]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:13][CH2:14][CH3:15])([O:11][CH2:22][CH3:23])[CH2:9][CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 226974'-ChloropropiophenoneHCID 31214Ethyl orthoformate

Product 1

HCID 22906421HCID 22906421, compoundYield 88%

Procedure

A solution of 15.0 g of p-chloropropiophenone and 7.8 mL of dry EtOH was treated with 22.0 mL of triethyl orthoformate. Gaseous HCl was bubbled through the solution until saturation and the reaction mixture heated to reflux overnight. An additional 14.8 mL of triethyl orthoformate was added and the reaction mixture allowed to cool to room temperature. The cooled mixture was washed with 10% Na2CO3, extracted with diethyl ether and concd in vacuo to afford 19.0 g (88%) of a crude orange/yellow oil. The oil was distilled and a fraction collected (75°-96° C., 100 mtorr) which contained 13.4 g of 1-chloro-4-(1,1-diethoxypropyl)benzene: μ (23,D) 1.5612; 1HNMR (CDCl3) δ 0.56 (t, 3H, 7.5 Hz), 1.19 (t, 6H, 7.0 Hz), 1.89 (q, 2H, 7.5 Hz), 3.36 (m, 4H), 7.28 (d, 2H, 8.5 Hz), 7.42 (d, 2H, 8.5 Hz). Anal. Calcd for C13H19O2Cl: C, 64.32; H, 7.89. Found: C, 64.09; H, 7.81.

Workup

  1. customGaseous HCl was bubbled through the solution until saturation
  2. temperaturethe reaction mixture heated
  3. temperatureto reflux overnight
  4. additionAn additional 14.8 mL of triethyl orthoformate was added
  5. washThe cooled mixture was washed with 10% Na2CO3
  6. extractionextracted with diethyl ether and concd in vacuo

Sources & evidence

ORD record
ord-f9c83f91f1f948ea99267f35893b6060
Source dataset
uspto-grants-1997_09
Patent number
US05672715

Reaction notes

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