Reaction #1929024

Reaction equation

sodium carbonate

triethylamine

Benzoyl chloride

→

4-(hydroxymethyl)phenyl benzoate

Yield 80.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGthe resulting solution was shaken at 0° C. for 5 hours
2. 2
   DryingThe organic phase was dried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Otherthe solvent was removed under reduced pressure
5. 5
   Otherthus affording a yellowish solid
6. 6
   Otherthat upon recrystallization from cyclohexane

Procedure

4-(Hydroxymethyll)phenol (1.087 g, 8.77 mmol) and triethylamine (1.3 mL, 8.77 mmol) were dissolved in 25 mL of dichloromethane. The solution was shaken at 0° C. for 30 minutes. Benzoyl chloride (1 mL, 8.77 mmol) was added drop by drop and the resulting solution was shaken at 0° C. for 5 hours. Saturated aqueous solution of sodium carbonate (20 mL) was added three times. The organic phase was dried over magnesium sulfate, filtered, and the solvent was removed under reduced pressure, thus affording a yellowish solid that upon recrystallization from cyclohexane provided 1.600 g (70.16 mmol, yield=80%) of 4-(hydroxymethyl)phenyl benzoate.

Source