Ethanol → Ethyl 3-fluoro-4-hydroxybenzoate

HRID 1361417Notes

Reaction equation

HRID 1361417 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH2:16](O)[CH3:17]>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH2:16][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 1604563-Fluoro-4-hydroxybenzoic acid

Product 1

HCID 13745619Ethyl 3-fluoro-4-hydroxybenzoateYield 100%

Conditions

Temperature
80 °C

Procedure

To a solution of 3-fluoro-4-hydroxybenzoic acid (Aldrich, 4.0 mmol, 624 mg) in ethanol (10 mL), was added thionyl chloride (2 mL, Aldrich). The reaction mixture was heated at 80° C. for 4 h, and concentrated in vacuo to remove the solvent and excess thionyl chloride to afford the desired product (736 mg, 100% yield) as a white solid. MS(ESI+) m/z 185.33 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove the solvent and excess thionyl chloride

Sources & evidence

ORD record
ord-73e0263a6e1545948f4a686e908c7c29
Source dataset
uspto-grants-2011_02
Patent number
US07880004B2

Reaction notes

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