Hydrochloric Acid → (E)-3-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)benzoic acid

HRID 422058Notes

Reaction equation

HRID 422058 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])=O.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][C:14]=1[CH3:22].[OH-].[K+].Cl>CO.O>[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])/[CH:20]=[CH:1]/[C:3]2[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=2)[C:6]([OH:8])=[O:7])=[CH:15][C:14]=1[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 120773-CarboxybenzaldehydeHCID 14797Potassium HydroxideHCID 701354'-Hydroxy-3'-methylacetophenone

Product 1

HCID 57831170(E)-3-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)benzoic acidYield 67.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-Formylbenzoic acid (15.0 g, 0.1 mol, Aldrich) and 4′-hydroxy-3′-methylacetophenone (15.0 g, 0.1 mol, Indofine) was dissolved in 150 mL of methanol and 50 mL of water. The solution was cooled with an ice-water bath, to which was added potassium hydroxide (28.0 g, 0.5 mol). The reaction mixture was stirred overnight. The resulted mixture was poured on to 600 mL of ice-water, acidified to pH=4-5 with 1 N HCl, filtered, washed with water (200 mL), methanol (100 mL) and dried in the air. 19 g (67%) of a solid was obtained as the desired (E)-3-(3-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)phenoxy)acetic acid. 1H NMR (400 MHz, DMSO-d6): 13.18 (br, 1H), 10.39 (s, 1H), 8.38 (s, 1H), 8.15 (m, 1H), 7.95 (m, 4H), 7.75 (d, 1H), 7.60 (m, 1H), 6.95 (d, 1H), 2.20 (s, 3H). MS (EI) for C17H14O4: 283 (MH+).

Workup

  1. temperatureThe solution was cooled with an ice-water bath, to which
  2. filtrationfiltered
  3. washwashed with water (200 mL), methanol (100 mL)
  4. customdried in the air

Sources & evidence

ORD record
ord-4884d5b00650418faf14c551c1d340e0
Source dataset
uspto-grants-2012_01
Patent number
US08101625B2

Reaction notes

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