Hydrochloric Acid → 4-(2-Chlorophenoxy)butanoic acid

HRID 341352Notes

Reaction equation

HRID 341352 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Br[CH2:10][CH2:11][CH2:12][C:13]([O:15]CC)=[O:14].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>CC(=O)CC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 72452-ChlorophenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 30143434-(2-Chlorophenoxy)butanoic acidYield 96.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
25 °C

Procedure

A 500 mL 3-neck round bottom flask equipped with a magnetic stirrer bar and a reflux condenser was charged with 12.88 g (100 mmol) of 2-chlorophenol, 22.54 g (110 mmol) of ethyl 4-bromobutyrate, 16.59 g, 120 mmol potassium carbonate and 350 mL of 2-butanone. The slurry was heated to reflux. After stirring for 21 hr at reflux, the reaction mixture was cooled to 25° C., filtered and concentrated. The residue was taken up in 400 mL of water and treated with 100 mL of 2N aqueous sodium hydroxide (200 mmol). The reaction mixture was heated to reflux for 120 min and cooled to 25° C. The resulting solution was acidified with aqueous 105 ml of 2N hydrochloric acid. The resulting white solid was isolated by filtration by washing with hexanes to yield 20.68 g of 4-(2-Chlorophenoxy)butanoic acid. Mp 85-87° C. Combustion analysis: Found: C, 55.97; H, 5.13%; Cl, 16.55%; C10H11ClO3 requires C, 55.96; H, 5.17%; Cl, 16.52%; 1H NMR (d6-DMSO): δ 12.1, bs, 1H (COOH); δ 7.42, dd, 1H, (H ortho to Cl); δ 7.29, t, 1H (H para to Cl); δ 7.13, d, 1H, (H ortho to OR); δ 6.95, t, 1H (H para to OR); δ 4.07, t, 2H, (CH2 α to O); δ 2.44, t, 2H (CH2 α to COOH); δ 1.98, p, 2H (CH2 β to ArO and COOH).

Workup

  1. customA 500 mL 3-neck round bottom flask equipped with a magnetic stirrer bar and a reflux condenser
  2. temperatureThe slurry was heated to reflux
  3. temperatureat reflux
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperatureThe reaction mixture was heated
  7. temperatureto reflux for 120 min
  8. temperaturecooled to 25° C
  9. customThe resulting white solid was isolated by filtration
  10. washby washing with hexanes

Sources & evidence

ORD record
ord-6a22ac29ae8842b0bc150edf500073e4
Source dataset
uspto-grants-2014_11
Patent number
US08895777B2

Reaction notes

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