Réaction #684951

Équation de réaction

sodium hydroxide

sodium borohydride

sulfuric acid

p-n-propylbenzoic acid

→

title compound

Rendement 90.1%

(4-Propylphenyl)methanol

Rendement 90.1%

Solvants

methanol

ether

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autrethe temperature of the reaction system below 20° C.
2. 2
   workup.ADDITIONwere added
3. 3
   Extractionthis mixture was extracted with ethyl acetate
4. 4
   LavageThe ethyl acetate layer was washed with saturated brine
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure

Mode opératoire

A solution of sodium borohydride (2.9 g, 76 mmol) and concentrated sulfuric acid in ether (prepared by adding 2.0 ml of concentrated sulfuric acid to 4.0 ml of ether) was added dropwise to a solution of p-n-propylbenzoic acid (5.0 g, 32 mmol) in tetrahydrofuran (20 ml) cooled to 0° C. keeping the temperature of the reaction system below 20° C., and then this mixture was stirred at room temperature for 3 hours. After the mixture was cooled on ice, methanol and 1 N sodium hydroxide were added, and this mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give the title compound (4.33 g). This compound was used in the following reaction without purification.

Source