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

HRID 566822Notes

Reaction equation

HRID 566822 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-83d8f30510774155a12e36a636e86bb0
Source dataset
uspto-grants-2001_01
Patent number
US06174915B1

Reaction notes

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