Hydrochloric Acid → HCID 22924469, compound

HRID 1662142Notes

Reaction equation

HRID 1662142 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[C:6]([OH:13])[CH:5]=1)[CH3:2].[C:14](OCC)(=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16].[O-]CC.[Na+].Cl>C(O)C.O.C(OCC)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:7]([C:10](=[O:12])[CH:11]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:13]2)=[CH:8][CH:9]=1)[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 27751631-(4-ethoxy-2-hydroxyphenyl)ethanone

Product 1

HCID 22924469HCID 22924469, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-(4-ethoxy-2-hydroxyphenyl)ethanone (Aldrich, 5.0 g, 27.7 mmol) and diethyl oxalate (8.3 mL, 61 mmol) in ethanol (50 mL) was added sodium ethoxide (21% in EtOH, 31 mL, 83 mmol) and the mixture was refluxed for 1.5 hours. The mixture was cooled to ambient temperature, diethyl ether (150 mL), water (150 mL) and 12N hydrochloric acid (7 mL) were added. The separated organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and was concentrated under reduced pressure to afford ethyl 7-ethoxy-4-oxo-4H-chromene-2-carboxylate. The intermediate was dissolved in acetic acid (70 mL) and 12N hydrochloric acid (8.5 mL), heated to reflux for 2 hours, and cooled to ambient temperature. Water (300 mL) was added and the solids were collected by filtration, rinsed with water, and freeze-dried to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.38 (t, 3H), 4.20 (q, 2H), 6.84 (s, 1H), 7.08 (dd, 1H), 7.19 (d, 1H), 7.92 (d, 1H). MS (APCI) m/z 235.04 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-4061246c75a74a1e917439e014fc205d
Source dataset
uspto-grants-2011_10
Patent number
US08030504B2

Reaction notes

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