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

HRID 2300005Notes

Reaction equation

HRID 2300005 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 0.5 M aqueous HCl (50 mL). The resultant pale orange perecipitate 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 perecipitate was filtered off
  3. washrinsed with water
  4. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-680f70529129470ead10fcddd612b977
Source dataset
uspto-grants-2002_12
Patent number
US06495699B2

Reaction notes

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