Hydrochloric Acid → 4-Fluoro-2-(hydroxymethyl)-6-[(phenylmethyl)oxy]phenol
Reaction equation
[F:1][C:2]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]2[O:6]C(C)(C)[O:8][CH2:9][C:4]=2[CH:3]=1.Cl>C(O)C>[F:1][C:2]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]([OH:6])=[C:4]([CH2:9][OH:8])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
To 6-fluoro-2,2-dimethyl-8-[(phenylmethyl)oxy]-4H-1,3-benzodioxine (9.9 g, 34.3 mmol) was added ethanol (50 mL) and 4 N HCl (aq) (50 mL). The mixture began as a suspension but became homogeneous while stirring for 20 min at 85° C. After cooling to rt, the ethanol was removed in vacuo, and the resulting aqueous mixture was extracted twice with ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo. 4-Fluoro-2-(hydroxymethyl)-6-[(phenylmethyl)oxy]phenol was isolated as a orange oil in quantitative yield. 1H NMR (400 MHz, CDCl3): δ 7.42-7.36 (m, 5H), 6.66-6.62 (m, 2H), 5.08 (s, 2H), 4.70 (s, 2H), 4.37 (br s, 2H).