Hydrochloric Acid → 2-(1-Benzofuran-2-yl)acetic acid

HRID 1106898Notes

Reaction equation

HRID 1106898 reaction equation
C[O:2][C:3](=[O:14])[CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1.O.[OH-].[Li+].CO.Cl>O1CCCC1.O.C(OCC)(=O)C.CCCCCCC>[O:6]1[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=[C:5]1[CH2:4][C:3]([OH:14])=[O:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 15618731Methyl 2-(benzofuran-2-yl)acetate

Product 1

HCID 111058882-(1-Benzofuran-2-yl)acetic acid

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

A solution of Example 8 (5.32 g, 28 mmol) and lithium hydroxide monohydrate (1.24 g, 30 mmol) in tetrahydrofuran (45 mL), water (30 mL), and methanol (12 mL) was stirred for 5 hours at room temperature. Water (60 mL) was added, and the reaction mixture was acidified to pH 4 using 2 M HCl and extracted with dichloromethane (5×150 mL). The organics were dried (MgSO4) and the solvent removed in vacuo. Column chromatography (ethyl acetate:heptane 4:1→ethyl acetate:methanol) gave a brown solid. This was dissolved in ethyl acetate, heptane was added, and the mixture was stirred overnight. Solvent was removed by syringe to give product as a pale brown solid, 17 mmol, 61%.

Workup

  1. extractionextracted with dichloromethane (5×150 mL)
  2. dry with materialThe organics were dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customColumn chromatography (ethyl acetate:heptane 4:1→ethyl acetate:methanol) gave a brown solid
  5. customSolvent was removed by syringe
  6. customto give product as a pale brown solid, 17 mmol, 61%

Sources & evidence

ORD record
ord-f88b56d56def4f608f6dc02c53aacccf
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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