Reaction #2069944

Reaction equation

sodium hydroxide

sodium borohydride

sulfuric acid

p-n-propylbenzoic acid

→

title compound

Yield 90.1%

(4-Propylphenyl)methanol

Yield 90.1%

Solvents

methanol

ether

tetrahydrofuran

Conditions

Workup

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

Procedure

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