Reaction #452453

Reaction equation

6-bromohexanoyl chloride

benzyl alcohol

→

Benzyl 6-bromohexanoate

Solvents

methylene chloride

pyridine

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled
2. 2
   Otherfor 90 min
3. 3
   ExtractionThe solution was extracted with 200 mL of 1 N HCl
4. 4
   Dryingthe solution dried over Na2SO4
5. 5
   FiltrationThe solution was filtered
6. 6
   Otherthe solvent removed in vacuo
7. 7
   Otherto give an oil
8. 8
   OtherThis oil was purified on silica gel
9. 9
   Washeluting with a gradient of chloroform in hexanes
10. 10
    workup.ADDITIONFractions containing the product (TLC Rf 0.52, CHCl3 /hexanes 6:4)
11. 11
    Otherthe solvent removed
12. 12
    Otherto give 24.4 g

Procedure

Benzyl 6-bromohexanoate was prepared by dropwise addition of a solution of 6-bromohexanoyl chloride (20.0 mL) in 100 mL of methylene chloride to a solution of 66.22 mL of benzyl alcohol in 60 mL of pyridine. The mixture was cooled using an ice-water bath for 90 min, then stirred at room temperature for 18 h. The solution was extracted with 200 mL of 1 N HCl followed by 2×150 mL of sat. NaHCO3. The extracts were discarded and the solution dried over Na2SO4. The solution was filtered and the solvent removed in vacuo to give an oil. This oil was purified on silica gel, eluting with a gradient of chloroform in hexanes. Fractions containing the product (TLC Rf 0.52, CHCl3 /hexanes 6:4) were combined and the solvent removed to give 24.4 g.

Source