Hydrochloric Acid → Methyl 4-[1,3-dioxo-3-[4-(pentyloxy)phenyl]propyl]benzoate

HRID 1596749Notes

Reaction equation

HRID 1596749 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:16](OC)(=[O:27])[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1.C[O-].[Na+].Cl>O.CN(C)C=O>[CH3:24][O:23][C:21]([C:20]1[CH:25]=[CH:26][C:17]([C:16](=[O:27])[CH2:14][C:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:12][CH:11]=2)=[O:15])=[CH:18][CH:19]=1)=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8441Dimethyl terephthalateHCID 79598p-(Pentyloxy)acetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 11405985Methyl 4-[1,3-dioxo-3-[4-(pentyloxy)phenyl]propyl]benzoateYield 61.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dimethylformamide (600 ml), p-pentyloxyacetophenone (60.0 g) and dimethyl terephthalate (73.5 g) were charged in 1-liter three-necked flask and stirred. To this mixture was added 28% methanolic solution (84.2 g) of sodium methoxide and, after that, a reaction was carried out at the inner temperature of 35 to 40° C. for 48 hours. After completion of the reaction, the reaction solution was added to a mixed solution of water (3,000 ml) and 1N hydrochloric acid (600 ml) to separate the crystals. The mixture was stirred at room temperature for 1 hour, and then the separated crystals were filtered. The wet crystals and methanol (1,000 ml) were charged in a 2-liter three-necked flask, heated to reflux for 2 hours and cooled down to room temperature, and the crystals were filtered. The crystals were washed with methanol (200 ml). The crystals were dried overnight in vacuo to give 1-(4-methoxycarbonyl-phenyl)-3-(4-pentyloxyphenyl)-propane-1,3-dione (66.0 g).

Workup

  1. customAfter completion of the reaction
  2. customto separate the crystals
  3. stirringThe mixture was stirred at room temperature for 1 hour
  4. filtrationthe separated crystals were filtered
  5. additionThe wet crystals and methanol (1,000 ml) were charged in a 2-liter three-necked flask
  6. temperatureheated
  7. temperatureto reflux for 2 hours
  8. filtrationthe crystals were filtered
  9. washThe crystals were washed with methanol (200 ml)
  10. customThe crystals were dried overnight in vacuo

Sources & evidence

ORD record
ord-199e9fbde9464fe79d401c9019093875
Source dataset
uspto-grants-2001_09
Patent number
US06291680B1

Reaction notes

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