Hydrochloric Acid → 1-(3,4-Dihydroxyphenyl)cyclopropanecarboxylic acid

HRID 1847302Notes

Reaction equation

HRID 1847302 reaction equation
[OH-:1].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([C:11]2([C:14]#N)[CH2:13][CH2:12]2)[CH:7]=[CH:8][C:9]=1[OH:10].Cl.[OH2:17]>>[OH:3][C:4]1[CH:5]=[C:6]([C:11]2([C:14]([OH:17])=[O:1])[CH2:13][CH2:12]2)[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 670436561-(3,4-Dihydroxyphenyl)cyclopropanecarbonitrile

Product 1

HCID 591293681-(3,4-Dihydroxyphenyl)cyclopropanecarboxylic acid

Procedure

To a solution of NaOH (20 g, 0.50 mol) in H2O (20 mL) was added 1-(3,4-dihydroxy-phenyl)-cyclopropanecarbonitrile (4.4 g, 25 mmol). The mixture was heated at reflux for 3 h before being cooled to room temperature. The mixture was neutralized with HCl (0.5 N) to pH 3-4 and extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with water, brine, dried over anhydrous MgSO4, and concentrated under vacuum to obtain 1-(3,4-dihydroxy-phenyl)-cyclopropanecarboxylic acid (4.5 g crude). From 900 mg crude, 500 mg pure 1-(3,4-dihydroxy-phenyl)-cyclopropanecarboxylic acid was obtained by preparatory HPLC. 1H NMR (DMSO, 300 MHz) δ 12.09 (br s, 1H), 8.75 (br s, 2H), 6.50-6.67 (m, 3H), 1.35-1.31 (m, 2H), 1.01-0.97 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. extractionextracted with ethyl acetate (20 mL×3)
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a8e6b2bba80a4825a21049d7896d1642
Source dataset
uspto-grants-2015_02
Patent number
US08952050B2

Reaction notes

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