Hydrogen Peroxide → 3-(2-Phenylethoxy)propan-1-ol

To a cooled (0° C.) solution of 2-allyloxyethylbenzene (5. g; 30.8 mmol) dissolved in THF (75 ml) is slowly added a 0.5M THF solution of 9-BBN [9-borabicyclo [3.3.1]nonane] (68 ml; 34 mmol) and the reaction mixture warmed to room temperature and stirred for 4 hours. The reaction mixture is then cooled to 0° C. and 5 ml H2O is added followed by slow addition of 6N NaOH (30 ml; 7.2 g/30 ml). After stirring for 5 minutes, 30% H2O2 (20 ml) is added over 15 min. The reaction mixture warms significantly but is kept from refluxing. After addition is complete, it is stirred for 15 minutes allowing the mixture to come to room temperature. It is then diluted with. Et2O, washed with H2O 2×, Na2S2O3 2×, NaHCO3 and brine, dried (MgSO4) and concentrated to dryness. The residue is purified by column chromatography using Et2O to obtain 3-(2-phenylethoxy)-1-propanol which is used directly in Step C.

1. temperatureThe reaction mixture is then cooled to 0° C.
2. stirringAfter stirring for 5 minutes
3. temperaturefrom refluxing
4. additionAfter addition
5. stirringit is stirred for 15 minutes
6. customto come to room temperature
7. additionIt is then diluted with
8. washEt2O, washed with H2O 2×, Na2S2O3 2×, NaHCO3 and brine
9. dry with materialdried (MgSO4)
10. concentrationconcentrated to dryness
11. customThe residue is purified by column chromatography

ORD record

ord-4082fa8a85f04045b3a89493fd8e88d9

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05455260