Hydrochloric Acid → Methyl 4-[1,3-dioxo-3-[4-(pentyloxy)phenyl]propyl]benzoate
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].[K+].C[CH2:22][CH2:23][CH:24]([O:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34]C=CC=1)=O)[CH3:25].Cl.O1CCC[CH2:38]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:22]=[CH:23][C:24]([O:26][CH2:27][CH2:28][CH2:30][CH2:35][CH3:34])=[CH:25][CH:38]=2)=[O:18])=[CH:11][CH:10]=1)=[O:7]Participants
6
Procedure
To a suspension of dimethyl terephthalate (1.94 g) and potassium 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-486626569dc843bdb3efbf78f07c5ea1
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06107458
Reaction notes
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