Hydrochloric Acid → HCID 18701970, compound

HRID 1990859Notes

Reaction equation

HRID 1990859 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[OH:13])[C:7]([OH:9])=[O:8])[CH3:2].Cl.[CH3:15]O>>[CH3:15][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:12]([OH:13])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 950853-Ethoxy-4-hydroxybenzoic acid

Product 1

HCID 18701970HCID 18701970, compoundYield 91%

Procedure

A solution of 3-ethoxy-4-hydroxy-benzoic acid (5.5 g, 30.19 mmol, 1.0 equiv) in methanol (300 mL) was saturated with anhydrous HCl gas and heated to reflux overnight. Evaporation of the solvent and purification of the crude reaction product over a short plug of silica eluting with dichloromethane yielded 5.4 g (91%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.37 (t, J=7.0 Hz, 3H), 3.80 (s, 3H), 4.08 (q, J=7.0 Hz, 2H), 6.11 (s, 1H), 6.86 (d, J=8.3 Hz, 1H), 7.45 (d, J=1.9 Hz, 1H), 7.54 (dd, J=8.3 Hz, J=1.9 Hz, 1H). 13C NMR (75 MHz, CDCl3): δ 14.69, 51.85, 64.74, 112.67, 114.05, 122.21, 124.05, 145.46, 150.20, 166.88. MS (ISN): 195.0 [M−H]−.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customEvaporation of the solvent and purification of the crude
  4. customreaction product over a short plug of silica eluting with dichloromethane

Sources & evidence

ORD record
ord-9debf052c1c34273965e40aea0936763
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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