Dichloromethane → Methyl 2-(4-acetylphenoxy)propanoate

HRID 1165344Notes

Reaction equation

HRID 1165344 reaction equation
[K].[CH3:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4].Br[CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15].C(Cl)Cl>CN(C)C=O.O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=1)(=[O:4])[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 74694'-HydroxyacetophenoneHCID 95576Methyl 2-bromopropionateHCID 5462222Potassium

Product 1

HCID 14717334Methyl 2-(4-acetylphenoxy)propanoateYield 76.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the potassium salt of 4-hydroxyacetophenone (8.8 g, 0.05 mol) in dimethylformamide (25 mL) is added methyl 2-bromopropanoate (10.2 g, 0.06 mol) over 30 minutes and stirred at 80°-90° C. for 4 hours under nitrogen. The reaction is cooled to room temperature and methylene chloride (75 mL) and water (75 mL) are added. The organic phase is separated, washed with water (100 mL), dried and concentrated to give methyl 2-(4-acetylphenoxy)propanoate (8.5 g) (yield 76%). Methyl 2-(4-acetylphenoxy)propanoate (7.0 g, 31.5 mmol) is combined with 2N NaOH (20 mL) and refluxed overnight. Water (30 mL) is added to the reaction which is then washed with methylene chloride (50 mL). It is then acidified to pH=1 with concentrated hydrochloric acid and extracted with ethyl acetate (3×100 mL). The organic phase is dried and concentrated to provide 2-(4 -acetylphenoxy)propanoic acid (5.0 g) (yield 92%): m.p. 104.3° C., IR (KBr) 3000 (br, vs), 2940 (br,s), 1754 (vs), 1650 (vs); 1H NMR (CDCl3) delta 1.69 (d, J=6.8 Hz, 3H), 2.55 (s,3H), 4.8 (q, J=6.8 Hz, 1H), 6.92 and 7.93 (dd, J=9.0 Hz, 4H).

Workup

  1. customThe organic phase is separated
  2. washwashed with water (100 mL)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-08843b1ef84a4d4283cf3f7d4d9cebb9
Source dataset
uspto-grants-1990_03
Patent number
US04908476

Reaction notes

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