Hydrochloric Acid → (E)-2-(3-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)phenoxy)acetic acid

HRID 884654Notes

Reaction equation

HRID 884654 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH2:7][C:8]([O:10]CC)=[O:9])=O.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][C:18]=1[CH3:26].[OH-].[K+].Cl>CO.O>[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])/[CH:24]=[CH:1]/[C:3]2[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=2)[O:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:19][C:18]=1[CH3:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 701354'-Hydroxy-3'-methylacetophenoneHCID 1494377Ethyl 2-(3-formylphenoxy)acetate

Product 1

HCID 57831167(E)-2-(3-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)phenoxy)acetic acidYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-(3-formylphenoxy)acetate (20.8 g, 0.1 mol) and 4′-hydroxy-3′-methylacetophenone (15.0 g, 0.1 mol) were 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 (21.0 g, 0.375 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, and extracted with ethyl acetate (4×200 mL). The combined organic layers were washed with water and brine (200 mL each), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The obtained yellow oil was dried under high-vacuum, 20 g (64%) of yellowish solid was obtained. 1H NMR (400 MHz, CDCl3): δ 9.95 (s, 1H), 8.40 (br, 1H), 7.80 (s, 1H), 7.65 (m, 2H), 7.22-7.55 (m, 5H), 6.85 (d, 1H), 4.75 (s, 2H), 2.22 (s, 3H). MS (EI): 313 (MH+).

Workup

  1. temperatureThe solution was cooled with an ice-water bath, to which
  2. extractionextracted with ethyl acetate (4×200 mL)
  3. washThe combined organic layers were washed with water and brine (200 mL each)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe obtained yellow oil was dried under high-vacuum

Sources & evidence

ORD record
ord-e8b9c0a3cf464af4b51344c6227d12cb
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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