Reaktion #80885

Reaktionsgleichung

NaOH

4-phenylbutyl bromide

methyl 4-hydroxybenzoate

NaOMe

→

title compound

Methyl 4-(4-Phenylbutoxy)benzoate

Lösungsmittel

DMF

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated at 60°-70° for 1 hr
2. 2
   TemperaturThe resulting mixture was heated at 60°-70° for 1 hr
3. 3
   workup.STIRRINGwith constant stirring
4. 4
   Temperaturcooled to room temperature
5. 5
   workup.ADDITIONwas added
6. 6
   Extraktionthe product was extracted twice with ethyl acetate (50 L and 80 L)
7. 7
   WaschenThe extracts were washed with 1N-NaOH (110 L) and saturated brine (20 L) successively
8. 8
   Einengenconcentrated to dryness in vacuo

Vorschrift

A solution of methyl 4-hydroxybenzoate (13.4 kg, 88 mol) in DMF (52 L) was added dropwise to a mixture of NaOMe (4.8 kg, 89 mol) and DMF (50 L) at room temperature under a gentle stream of nitrogen. The reaction mixture was heated at 60°-70° for 1 hr with stirring and then cooled to room temperature. To this mixture was added dropwise a solution of 4-phenylbutyl bromide (16.92 kg, 79.4 mol) in DMF (5 L). The resulting mixture was heated at 60°-70° for 1 hr with constant stirring and cooled to room temperature. After an addition of 1N-NaOH (110 L) was added, and the product was extracted twice with ethyl acetate (50 L and 80 L). The extracts were washed with 1N-NaOH (110 L) and saturated brine (20 L) successively, and then concentrated to dryness in vacuo to give the title compound in quantitative yield.

Quelle