Hydrochloric Acid → Methyl 4-ethoxy-2-hydroxybenzoate

HRID 703042

Reaction equation

HRID 703042 reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([OH:14])[CH:6]=1)[CH3:3].[CH3:15]O>>[CH2:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH3:15])=[O:10])=[C:7]([OH:14])[CH:6]=1)[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 826284-Ethoxysalicylic acid

Product 1

HCID 4389058Methyl 4-ethoxy-2-hydroxybenzoate

Conditions

Temperature
15 °C

Procedure

Hydrogen chloride was bubbled into a stirred solution of 4-ethoxy-2-hydroxybenzoic acid (10.10 g. 0.554 mol) in methanol (2000 mL) until the solution was saturated. The solution was heated under reflux for 3 days and then cooled to 15° C. This caused the product to crystallize out. The crystals were collected, rinsed with methanol and hexanes, and dried. Methyl 4-ethoxy-2-hydroxybenzoate was obtained as a pale amber solid (49.3 g) melting at 77°-78° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 3 days
  3. customto crystallize out
  4. customThe crystals were collected
  5. washrinsed with methanol and hexanes
  6. customdried

Sources & evidence

ORD record
ord-4f854a3ac4ac4c6dbad1cb6cdc558703
Source dataset
uspto-grants-1991_01
Patent number
US04981509

Linked notes

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