Hydrochloric Acid → 4-Fluoro-2-(hydroxymethyl)-6-[(phenylmethyl)oxy]phenol

HRID 253279Notes

Reaction equation

HRID 253279 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]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 668895716-fluoro-2,2-dimethyl-8-[(phenylmethyl)oxy]-4H-1,3-benzodioxine

Product 1

HCID 668904684-Fluoro-2-(hydroxymethyl)-6-[(phenylmethyl)oxy]phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. temperatureAfter cooling to rt
  2. customthe ethanol was removed in vacuo
  3. extractionthe resulting aqueous mixture was extracted twice with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1ddeb3fe7ae4b0f868ed46137a0b000
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

Loading…