2-Phenylethanol → 4-(2-Phenylethoxy)phenylacetonitrile

Diethylazodicarboxylate (DEAD, 7.85 g, 45.1 mmol), was added to a solution of 4-hydroxybenzyl cyanide (5.0 g, 37.6 mmol), phenethylalcohol (5.04 g, 41.3 mmol), and triphenylphosphine (11.82 g, 45.1 mmol) in anhydrous THF (100 mL) at room temperature. A water bath was used to maintain the temperature of the exothermic reaction near ambient. The water bath was removed after 40 minutes and the yellow solution stirred 24 hours. Water was added and the mixture extracted with ether (3×100 mL). The combined organic layers were washed with water (2×75 mL), brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give an oily yellow solid. The residue was washed with ether, and the resulting white solid removed by filtration. The filtrate was concentrated in vacuo to give a yellow oil, which was purified by chromatography on silica gel with elution by EtOAc/hexanes (2:8) to give the desired product (5.87 g, 66%) as a light yellow oil.

1. customA water bath was used
2. temperatureto maintain
3. customthe temperature of the exothermic reaction near ambient
4. customThe water bath was removed after 40 minutes
5. additionWater was added
6. extractionthe mixture extracted with ether (3×100 mL)
7. washThe combined organic layers were washed with water (2×75 mL), brine
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated in vacuo
10. customto give an oily yellow solid
11. washThe residue was washed with ether
12. customthe resulting white solid removed by filtration
13. concentrationThe filtrate was concentrated in vacuo
14. customto give a yellow oil, which
15. customwas purified by chromatography on silica gel with elution by EtOAc/hexanes (2:8)

ORD record

ord-5812ac0468a14c688220edc1c0efaf83

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04895862