2-Phenylethanol → Phenethyl Benzoate

HRID 1374482Notes

Reaction equation

HRID 1374482 reaction equation
[C:1]([O:9][CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]1([CH2:17]CO)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:1]([O:9][CH2:10][CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 60542-PhenylethanolHCID 7150Methyl Benzoate

Product 1

HCID 7194Phenethyl BenzoateYield 81%

Conditions

Temperature
210 °C

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.

Workup

  1. distillation230 g of distillate was collected
  2. customThe methanol was stripped from the distillate on a Buchi rotary evaporator
  3. customwas collected
  4. temperatureThe batch was heated for 2 h at 210° C. and 2 h at 220° C., whereupon 40 g of distillate
  5. customwas collected
  6. customThe 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. additionwas treated with activated carbon as usual

Sources & evidence

ORD record
ord-c8ad3843ea6d484a9585b462a45d391f
Source dataset
uspto-grants-2007_01
Patent number
US07166275B2

Reaction notes

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