Potassium Carbonate → HCID 11565461, compound

HRID 2390601Notes

Reaction equation

HRID 2390601 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:18][C:19](=[O:24])[CH2:20][CH2:21][CH2:22]Br)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:22][CH2:21][CH2:20][C:19]([OH:24])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 804592-Benzyloxyphenol

Product 1

HCID 11565461HCID 11565461, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 250 mL flask, equipped with a reflux condenser, magnetic stirrer, and under inert atmosphere, was added 2-benzyloxy-phenol (8.0 g, 40 mmol), 4-bromobutanoic acid ethyl ester (5.7 mL, 40 mmol), potassium carbonate (7.2 g, 52 mmol), and ethanol (100 mL). The reaction mixture was heated to reflux with stirring for 8 hours. The reaction was cooled to room temperature and the insoluble byproduct was removed by suction filtration. 2N aqueous sodium hydroxide (30 mL) was added to the filtrate. This solution was heated to 50° C. for 2 hours. The solution was cooled to room temperature, the ethanol removed under reduced pressure, and the resulting solution was adjusted to pH 9. The aqueous solution was washed with ethyl acetate (2×30 mL) and residual ethyl acetate was removed under reduced pressure. The solution was cooled to 0° C. with an external ice bath and then acidified to pH 2 with 6N aqueous hydrochloric acid. The precipitated product was collected by suction filtration and dried under vacuum. The product (7.2 g, 63%) was isolated as a white powder. 1H-NMR (400 MHz, DMSO-d6): δ 12.0, s, 1H(COOH); δ 7.4, multiplet, 5H (Benzylic aryl H's); δ 7.0, multiplet, 2H (Aryl H's); δ 6.9, multiplet, 2H (Aryl H's); δ 5.0, s, 2H (Benzylic CH2); δ 4.0, t, 2H (CH2 α to phenoxy); δ 2.4, t, 2H(CH2 α to COOH); δ 1.9, multiplet, 2H (remaining CH2 group).

Workup

  1. customTo a 250 mL flask, equipped with a reflux condenser, magnetic stirrer
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. customthe insoluble byproduct was removed by suction filtration
  5. addition2N aqueous sodium hydroxide (30 mL) was added to the filtrate
  6. temperatureThis solution was heated to 50° C. for 2 hours
  7. temperatureThe solution was cooled to room temperature
  8. customthe ethanol removed under reduced pressure
  9. washThe aqueous solution was washed with ethyl acetate (2×30 mL) and residual ethyl acetate
  10. customwas removed under reduced pressure
  11. temperatureThe solution was cooled to 0° C. with an external ice bath
  12. filtrationThe precipitated product was collected by suction filtration
  13. customdried under vacuum

Sources & evidence

ORD record
ord-7b065751152e4f489791aab804b6a89a
Source dataset
uspto-grants-2012_09
Patent number
US08273794B2

Reaction notes

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