Hydrochloric Acid → 1,5-Di(2-furyl)-3-(2,4-dimethoxyphenyl)-1,5-pentanedione

HRID 5549

Reaction equation

HRID 5549 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[C:13]([C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)(=[O:15])[CH3:14].[OH-:21].[K+].Cl>CO.O>[O:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:13](=[O:15])[CH2:14][CH:5]([C:4]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:3]=1[O:2][CH3:1])[CH2:14][C:13]([C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 145052-AcetylfuranHCID 14797Potassium HydroxideHCID 691752,4-Dimethoxybenzaldehyde

Product 1

HCID 150019121,5-Di(2-furyl)-3-(2,4-dimethoxyphenyl)-1,5-pentanedione

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Following the general methods outlined by Weller and Luellen (see above), to a solution of 16.6 g (0.1 mole) of 2,4-dimethoxybenzaldehyde 1 and 20 ml (0.2 mole) of 2-acetylfuran 2 in 100 ml of methanol was added 5.5 g of potassium hydroxide previously dissolved in a small amount of methanol. The resulting mixture was heated to reflux and then stirred overnight at 55° C. The solution was then poured into water acidified with 1N HCl and extracted with CH2Cl2. The CH2Cl2 extracts were dried (Na2SO4) and the solvents removed at high vacuum. The resulting amber oil solidified on standing overnight affording 36.7 g of crude dione 3.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. extractionextracted with CH2Cl2
  4. dry with materialThe CH2Cl2 extracts were dried (Na2SO4)
  5. customthe solvents removed at high vacuum
  6. waiton standing overnight
  7. customaffording 36.7 g of crude dione 3

Sources & evidence

ORD record
ord-a5d5033460474ef09b7089853a326df4
Source dataset
uspto-grants-1993_09
Patent number
US05245038

Linked notes

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