Hydrochloric Acid → HCID 68535696, compound

HRID 341347Notes

Reaction equation

HRID 341347 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1O.BrC[CH2:11][CH2:12][C:13]([O:15][CH2:16]C)=O.[C:18](=[O:21])([O-])[O-:19].[K+].[K+].[OH-].[Na+].Cl>CC(=O)CC.O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][O:15][CH2:13][CH2:12][CH2:11][C:18]([OH:19])=[O:21]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 335O-CresolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 76300Ethyl 4-bromobutyrate2×

Product 1

HCID 68535696HCID 68535696, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-methylphenol (16.22 g, 0.15 mol), ethyl 4-bromobutanoate (33.80 g, 0.165 mol), and potassium carbonate (24.88 g, 0.18 mol) in 500 mL of 2-butanone was heated at reflux under nitrogen for 5 hours An additional 3 g of ethyl 4-bromobutanoate was added, and the reflux was continued for an additional 25 h. The reaction was allowed to cool to room temperature. Water and ethyl acetate were added. The organic product was extracted into the organic layer. The organic layer was separated and washed with water and brine. It was concentrated in vacuo to yield an oil. 200 mL of water and 150 mL of a 2N aqueous solution of NaOH was added to the oil. The mixture was stirred at room temperature overnight, and then heated at reflux for an hour. The mixture was cooled to room temperature and ice was added to chill the mixture to about 0° C. Slow addition of a solution of 2N hydrochloric acid solution (150 ml) caused an immediate precipitation. The resulting solid was collected by filtration, washed successively with water and with heptane. Drying in vacuo provided 22.18 g (76%) of the title compound as a white solid. Mp: 79-80° C. HPLC Rt 4.96 min.; 1H NMR (DMSO d6, 300 MHz) δ: 1.97 (m, 2H), 2.15 (s, 3H), 2.42 (t, 2H), 3.97 (t 2H), 6.82 (t, 1H), 6.88 (d, 1H), 7.10-7.16 (m, 2H), 12.20 (s, 1H). Anal. Calcd for C11H14O3: C, 68.02; H, 7.27. Found: C, 68.04; H, 7.15.

Workup

  1. temperaturewas heated
  2. additionwas added
  3. extractionThe organic product was extracted into the organic layer
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. concentrationIt was concentrated in vacuo
  7. customto yield an oil
  8. temperatureheated
  9. temperatureat reflux for an hour
  10. temperatureThe mixture was cooled to room temperature
  11. additionice was added
  12. temperatureto chill the mixture to about 0° C
  13. customan immediate precipitation
  14. filtrationThe resulting solid was collected by filtration
  15. washwashed successively with water and with heptane
  16. customDrying in vacuo

Sources & evidence

ORD record
ord-5f1973a8379740c1b9aaacf1a4e807ee
Source dataset
uspto-grants-2014_11
Patent number
US08895777B2

Reaction notes

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