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

HRID 1386592Notes

Reaction equation

[C:1]([O:13]C)(=O)[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C[C:16]([CH3:19])([O-:18])[CH3:17].C[CH2:21][CH2:22][CH:23]([O:25][CH2:26][C:27]([C:29]1[CH:34]=[CH:33]C=CC=1)=O)[CH3:24].Cl.O1CCC[CH2:37]1>>[CH3:9][O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([C:1](=[O:13])[CH2:17][C:16]([C:19]2[CH:21]=[CH:22][C:23]([O:25][CH2:26][CH2:27][CH2:29][CH2:34][CH3:33])=[CH:24][CH:37]=2)=[O:18])=[CH:11][CH:10]=1)=[O:7]

Participants

Reactant 5

HCID 313Hydrochloric Acid

HCID 8028Tetrahydrofuran2×

HCID 8441Dimethyl terephthalate

HCID 45749132-Methylpropan-2-olate

HCID 539231554-Pentyloxyacetophenone

Product 1

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

Procedure

To a suspension of dimethyl terephthalate (1.94 g) and potassiuim t-butoxide (2.24 g) in tetrahydrofuran (30 ml) was added 4-pentyloxyacetophenone (1.59 g) in tetrahydrofuran (10 ml) at 70° C. dropwise. The mixture was refluxed for 30 minutes and poured into 1N HCl (50 ml). The mixture was extracted with ethyl acetate (100 ml) and the organic layer was washed with H2O (100 ml), brine (100 ml) and evaporated under reduced pressure. The residue was triturated with acetonitrile (20 ml), collected by filtration and dried under reduced pressure to give 1-(4-Methoxycarbonylphenyl)-3-(4-pentyloxyphenyl)propane-1,3-dione (2.41 g) as yellow solid.

Workup

temperatureThe mixture was refluxed for 30 minutes
extractionThe mixture was extracted with ethyl acetate (100 ml)
washthe organic layer was washed with H2O (100 ml), brine (100 ml)
customevaporated under reduced pressure
customThe residue was triturated with acetonitrile (20 ml)
filtrationcollected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-1df928ddd4914ed29f9064850d8554b6
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265536B1

Reaction notes

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