Reaction #2200605

Reaction equation

2-Chloroacetophenone

(+) DIP-chloride

diethanolamine

→

2-chloro-1-phenylethanol

Solvents

THF

Conditions

Workup

1. 1
   OtherTHF was removed in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ether (210 mL)
3. 3
   FiltrationThe separated solid was filtered
4. 4
   Washthe filtered cake was washed with ether (150 mL)
5. 5
   OtherThe combined filtrates were evaporated to dryness
6. 6
   Otherto give 15.53 g
7. 7
   OtherThis was purified by silica gel column chromatography

Procedure

2-Chloroacetophenone (6.25 g., 40.4 mmol) was treated with (+) DIP-chloride (18 g., 56.1 mmol) in anhydrous THF (40 mL) at dry-ice bath temperature and left overnight. The temperature was raised to room temperature and THF was removed in vacuo. The residue was dissolved in ether (210 mL). The diethanolamine (9 g., 8 5.6 mmol) was added and the mixture stirred at room temperature for 5 hrs. The separated solid was filtered and the filtered cake was washed with ether (150 mL). The combined filtrates were evaporated to dryness to give 15.53 g. of crude product. This was purified by silica gel column chromatography using 1% ether and petroleum ether 4.32 g (68%) of the desired product as an oil.

Source