Ethanol → Ethyl 4-fluoro-2-hydroxybenzoate

HRID 1483649Notes

Reaction equation

HRID 1483649 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[OH:11])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 676614-Fluorosalicylic acid

Product 1

HCID 22478444Ethyl 4-fluoro-2-hydroxybenzoateYield 85%

Conditions

Temperature
120 °C

Procedure

To a solution of 4-fluoro-2-hydroxybenzoic acid compound 3 (20.0 g, 128.11 mmol) in ethanol (100 mL) was added conc. sulfuric acid (10 mL). The resulting mixture was heated in a 120° C. oil bath O/N. The solvent was removed under reduced pressure to give crude product, which was purified by column chromatography (silica gel, 10% EtOAc in hexane) to afford the title compound 4 (19.9 g, 85%) as a colorless solid. 1H NMR 400 MHz (CDCl3) δ: 11.15 (s, 1H), 7.83 (d, J=6.6 Hz, 1H), 7.81 (d, J=6.6 Hz, 1H), 6.62 (dd, J=10.1, 2.3 Hz, 1H), 6.61 (dd, J=7.0, 2.0 Hz, 1H), 4.41 (q, J=7.0 Hz, 2H), 1.42 (t, J=7.0 Hz, 3H); MS (ES) m/z: 185 (M+1)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give crude product, which
  3. customwas purified by column chromatography (silica gel, 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-c1d22702e8d94672911cb7fb0f11976d
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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