Reaction #725873

Reaction equation

methyl benzoate

2-phenylethyl alcohol

→

2-phenylethyl benzoate

Yield 81.0%

Conditions

Workup

1. 1
   workup.DISTILLATION230 g of distillate was collected
2. 2
   OtherThe methanol was stripped from the distillate on a Buchi rotary evaporator
3. 3
   Otherwas collected
4. 4
   TemperatureThe batch was heated for 2 h at 210° C. and 2 h at 220° C., whereupon 40 g of distillate
5. 5
   Otherwas collected
6. 6
   OtherThe excess 2-phenylethyl alcohol (3.5% by GLC) and methyl benzoate (2.7% by GLC) were removed by vacuum distillation as usual and the product
7. 7
   workup.ADDITIONwas treated with activated carbon as usual

Procedure

The reaction was set up as in Example 2 except that methyl benzoate (748.8 g, 5.50 mol) was used instead of benzoic acid and 671.9 g (5.50 mol) of 2-phenylethyl alcohol was used. After 4 h at 190° C., 230 g of distillate was collected and the reaction mixture was 51% product by GLC. The methanol was stripped from the distillate on a Buchi rotary evaporator and the residue was returned to the reaction flask. The batch was heated for 2 h at 200° C. and 2 h at 210° C., whereupon 170 g of distillate was collected and the reaction mixture was 80% product by GLC. The methanol was stripped from the distillate as before, and the residue was returned to the reaction flask. The batch was heated for 2 h at 210° C. and 2 h at 220° C., whereupon 40 g of distillate was collected and the reaction mixture was 94% product by GLC. The excess 2-phenylethyl alcohol (3.5% by GLC) and methyl benzoate (2.7% by GLC) were removed by vacuum distillation as usual and the product was treated with activated carbon as usual to afford 1000 g (81%) of 2-phenylethyl benzoate. The residual 2-phenylethyl alcohol was 0.30, the APHA color was 40, the acid number was 0.13 mg KOH/g, the saponification number was 245 mg KOH/g, and the residual tin was <10 ppm.

Source