Phosphoric Acid → 4-Propyl 1-(3-methoxy-2-propen-1-yl)benzene
Reaction equation
[CH3:1][O:2][CH:3](OC)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH3:14])=[CH:8][CH:7]=1.P(=O)(O)(O)O.N1C=CC=CC=1>CO>[CH2:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH:4]=[CH:3][O:2][CH3:1])=[CH:11][CH:10]=1)[CH2:13][CH3:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A reaction flask was charged with 3-(4-propyl-phenyl)-propionaldehyde (147 g, prepared as above), methanol (500 mL), and TMOF (90 g). The reaction mass was cooled to 0° C. and hydrochloric acid (37%, 1 g) was added in one portion. The reaction was exothermic and the temperature rose to 23° C. The reaction mass was quenched with sodium methoxide in methanol (25%, 10 g) and the solvent was removed by evaporation. The crude intermediate product 3-(4-propyl-phenyl)-propionaldehyde dimethylacetal was provided and confirmed by the NMR analysis. 3-(4-Propyl-phenyl)-propionaldehyde dimethylacetal was further treated with phosphoric acid (10 g) and pyridine (8 g) at 200° C. The reaction mass was aged for 4 hours, during which methanol was recovered in a Dean Stark trap. The reaction mass was then cooled and washed with aqueous sodium carbonate solution. Fractional distillation of the organic layer afforded the product 4-propyl 1-(3-methoxy-2-propen-1-yl)benzene (80 g), which had a boiling point of 101° C. at a pressure of 3 mmHg.
Workup
- customwas recovered in a Dean Stark trap
- temperatureThe reaction mass was then cooled
- washwashed with aqueous sodium carbonate solution
- distillationFractional distillation of the organic layer
Sources & evidence
- ORD record
- ord-60ddf8e2a57d480eaef13e6e8c650486
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168834B2
Reaction notes
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