Hydrochloric Acid → HCID 24772034, compound

HRID 341353Notes

Reaction equation

HRID 341353 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].Br[CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>CC(=O)CC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 76300Ethyl 4-bromobutyrateHCID 182387Phenol, 2-fluoro-5-methyl-

Product 1

HCID 24772034HCID 24772034, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
25 °C

Procedure

A 200 ml 3-neck round bottom flask equipped with a magnetic stirrer bar and a reflux condenser was charged with 4.99 g (40 mmol) of 2-fluoro-5-methyl phenol, 9.01 g (44 mmol) of ethyl 4-bromobutyrate, 6.63 g (48 mmol) potassium carbonate and 120 ml of 2-butanone. The slurry heated to reflux. After stirring for 14.5 hr at reflux, the reaction mixture was cooled to 25° C., filtered and concentrated. The residue was taken up in water (200 ml) and treated with 42 ml (84 mmol) 2N aqueous sodium hydroxide. The reaction mixture was heated to reflux for 2 hours and cooled to 25° C. The yellow solution was acidified with 45 ml 2N aqueous hydrochloric acid. The resulting white solid was isolated by filtration washing with twice with water then twice with hexanes to yield 7.64 g (90%), mp 62-64° C. Combustion analysis: Found: C, 62.2%; H, 6.19%; Calculated: C, 62.26%; H, 6.17%; 1H NMR analysis (d6-DMSO): δ 12.2, broad s, 1H, (COOH); δ7.0, m, 2H (aryl H); δ 6.7, s, 1H (aryl H); δ 4.0, t, 2H (CH2 α ArO); δ 2.4, t, 2H (CH2 α COOH); δ 2.21, s, 3H (CH3 para F); δ 1.90, m, 2H (CH2 β COOH).

Workup

  1. customA 200 ml 3-neck round bottom flask equipped with a magnetic stirrer bar and a reflux condenser
  2. temperatureThe slurry heated to reflux
  3. temperatureat reflux
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperatureThe reaction mixture was heated
  7. temperatureto reflux for 2 hours
  8. temperaturecooled to 25° C
  9. customThe resulting white solid was isolated by filtration
  10. washwashing with twice with water
  11. customtwice with hexanes to yield 7.64 g (90%), mp 62-64° C

Sources & evidence

ORD record
ord-b6d17e2b3dc84453b463b605439f2581
Source dataset
uspto-grants-2014_11
Patent number
US08895777B2

Reaction notes

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