Hydrochloric Acid → 2-(2-Biphenyl-4-yl-furan-5-yl)-acetic acid

HRID 613930Notes

Reaction equation

HRID 613930 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)C.[Li+].[OH-].Cl>C1COCC1>[C:14]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:15]=[CH:16][C:11]([C:9]2[O:10][C:6]([CH2:5][C:4]([OH:23])=[O:3])=[CH:7][CH:8]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 183415102-(2-Biphenyl-4-yl-furan-5-yl)-acetic acid ethyl ester

Product 1

HCID 183803012-(2-Biphenyl-4-yl-furan-5-yl)-acetic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-biphenyl-4-yl-furan-5-yl)-acetic acid ethyl ester (0.465 g, 1.44 mmol) in THF (10 mL) at 0° C. was added 2M aqueous LiOH (2 mL). The mixture was allowed to warm over 4 hours to ambient temperature and then poured into 0.5M aqueous HCl (50 mL). The resultant pale orange precipitate was filtered off, rinsed with water, and dried under vacuum over P2O5 to provide 400 mg (100%) of 2-(2-biphenyl-4-yl-furan-5-yl)-acetic acid as a light orange solid, mp 196-210° C., used without further purification. 1H NMR (acetone-d6): δ 7.78 (d, 2H, J=8.1 Hz), 7.72-7.67 (m, 4H), 7.46 (t, 2H, J=7.4 Hz), 7.35 (t, 1H, J=7.4 Hz), 6.84 (d, 1H, J=3.3 Hz), 6.41 (d, 1H, J=3.3 Hz), 3.81 (s, 2H). Anal. Calculated for C18H14O3 : C, 77.68; H, 5.07. Found: C, 77.44; H, 5.16.

Workup

  1. temperatureto warm over 4 hours to ambient temperature
  2. filtrationThe resultant pale orange precipitate was filtered off
  3. washrinsed with water
  4. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-55fb6bccc65b4f3f932b55d89dc79408
Source dataset
uspto-grants-1999_12
Patent number
US06008243

Reaction notes

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