Chlorobutyl Benzoate

In a 200-ml. round-bottomed flask fitted with an eflacient reflux condenser are mixed 31.4 ml, (38 g., 0.27 mole) of freshly distilled benzoyl chloride, 28.2 ml, (25 g., 0.35 mole) of tetra-hydrofuran (Note 1), and 5 g. of freshly fused zinc chloride. A vigorous reaction begins immediately, and after a few seconds, when the mixture starts to boil, external cooling is applied with an ice bath. After the initial reaction has subsided, the mixture is heated on a steam bath for 15 minutes, cooled, and dissolved in 100 ml. of benzene. The benzene solution is washed with 100 ml. of a 5% solution of sodium chloride and then with 100 

Good-quality commercial tetrahydrofuran may be used as received, or redistilled b.p. 65-66°. 

The product develops a slight yellow tint on standing. 

---

Chlorobutyl benzoate has been prepared by the action of benzoyl chloride on tetrahydrofuran in the presence of titanium chloride, stannic chloride, or zinc chloride. ... 

Oxide fission. Benzoyl chloride reacts with tetrahydrofurane in the presence of a catalytic amount of zinc chloride to give 4-chlorobutyl benzoate. The reaction is... 

Figure 1. Conversion versus time for substitution by tetrabutylammonium benzoate on poly(epichlorohydrin) (A, A, separate runs) poly[(2-chloroethyl)-oxirane] (O) poly[(3-chloropropyl)oxirane] (V) and poly[(4-chlorobutyl)-oxirane] ( ). (Reproduced with permission from ref. 1. Copyright 1982 Wiley.)...

---