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

HRID 1816779Notes

Reaction equation

HRID 1816779 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.CC(C)([O-])C.[K+].Cl>CO.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 23665647Potassium tert-butoxide

Product 1

HCID 11405985Methyl 4-[1,3-dioxo-3-[4-(pentyloxy)phenyl]propyl]benzoateYield 91.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Dimethylformamide (485 l), p-pentyloxyacetophenone (30.3 kg) and dimethyl terephthalate (45.6 kg) were charged in 2000-liter reactor and stirred. To this mixture was added potassium tert-butoxide (24.7 kg) in several portions and, after that, a reaction was carried out at the inner temperature of 20 to 25° C. for 3.5 hours. After completion of the reaction, methanol (1210 l) was added to the reaction solution at 20 to 30° C. and then 6N hydrochloric acid (49 l) at 5 to 15° C. The mixture was stirred at room temperature for 1 hour, and the resulting appeared crystals were filtered and washed with methanol (152 l) and then water (152 l). The crystals were dried overnight in vacuo to give 1-(4-methoxycarbonylphenyl)-3-(4-pentyloxyphenyl)propane-1,3-dione (49.6 kg).

Workup

  1. additionwas added to the reaction solution at 20 to 30° C.
  2. customat 5 to 15° C
  3. stirringThe mixture was stirred at room temperature for 1 hour
  4. filtrationwere filtered
  5. washwashed with methanol (152 l)
  6. customThe crystals were dried overnight in vacuo

Sources & evidence

ORD record
ord-fe417f63de9c4f2da0b55b26a58b4c7e
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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