Reaction #499075

Reaction equation

2-ethyl-1-hexanol

triethylamine

2-phenylacetyl chloride

→

2-phenylacetic acid

Solvents

methylene chloride

Conditions

Workup

1. 1
   Filtrationfilter
2. 2
   Washwash the filtercake with methylene chloride (50 mL)
3. 3
   WashCombine the organic phases and wash with 5% aqueous hydrochloric acid (50 mL) and water
4. 4
   DryingDry (MgSO4)
5. 5
   Otherevaporate the solvent in vacuo
6. 6
   workup.DISTILLATIONpurify by distillation

Procedure

Mix 2-ethyl-1-hexanol (6.5 g, 5 mol), triethylamine (50.5 g, 0.5 mol) and methylene chloride (50 mL). Add, by dropwise addition, 2-phenylacetyl chloride (5 mol) and warm to 50° C. Stir at room temperature overnight, filter and wash the filtercake with methylene chloride (50 mL). Combine the organic phases and wash with 5% aqueous hydrochloric acid (50 mL) and water. Dry (MgSO4), evaporate the solvent in vacuo and purify by distillation to give 2-phenylacetic acid, 2-(2-ethylhexy)l ester.

Source