Hydrochloric Acid → 2-(4-Vinylphenyl)ethanol

Temperature

0 °C

To a VP-MgCl solution as prepared in Example 12 of this section was added a solution of 4.84 g ethylene oxide (0.11 mol) in 50 ml THF. The solution was added via additional funnel over one hour, maintaining the reaction mixture at 0° C. Keep stir at 0° C. for one more hour after the addition was finished. The reaction was then stirred for an additional 1 h at 0° C. 60 ml of 2 M aqueous hydrochloric acid (HCl) solution was added via the addition funnel, maintaining the temperature below 20° C. The reaction was filtered and extracted two times with 100 mL of diethyl ether. The organic phases were combined, dried over MgSO4 and filtered. The diethyl ether was removed by vacuum evaporation at room temperature. 11.2 g white waxy solid, 75.7%). 1H NMR (DMSO-d6): δ 7.20-δ 7.40 (m, 4H, aromatic), δ 6.72 (m, 1H, vinyl), δ 5.75 (d, 1H, vinyl), δ 5.23 (d, 1H, vinyl), δ 4.70 (t, 1H, OH), δ 3.65 (t, 2H, CH2—O), δ 2.72 (t, 2H, CH2—C).

1. customTo a VP-MgCl solution as prepared in Example 12 of this section
2. additionThe solution was added via additional funnel over one hour
3. additionafter the addition
4. stirringThe reaction was then stirred for an additional 1 h at 0° C
5. temperaturemaintaining the temperature below 20° C
6. filtrationThe reaction was filtered
7. extractionextracted two times with 100 mL of diethyl ether
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customThe diethyl ether was removed by vacuum evaporation at room temperature

ORD record

ord-1c074f39c9754acd86be445a11a70a0f

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07396880B2