Hydrochloric Acid → 2-(1-Benzofuran-3-yl)acetic acid

HRID 1106896Notes

Reaction equation

HRID 1106896 reaction equation
C[O:2][C:3](=[O:14])[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH:6]=1.O.[OH-].[Li+].CO.Cl>O1CCCC1.O.C(OCC)C.CCCCCCC>[O:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:5]([CH2:4][C:3]([OH:14])=[O:2])=[CH:6]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 10976279Methyl Benzofuran-3-acetate

Product 1

HCID 27629402-(1-Benzofuran-3-yl)acetic acid

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

A solution of Example 6 (6.23 g, 33 mmol) and lithium hydroxide monohydrate (1.45 g, 35 mmol) in tetrahydrofuran (50 mL), water (35 mL), and methanol (14 mL) was stirred for 6.5 hours at room temperature. Water (70 mL) was added, and the reaction mixture was acidified to pH 4 using 2 M HCl and extracted with dichloromethane (5×200 mL). The organics were dried (MgSO4) and the solvent removed in vacuo to give a brown solid. This was dissolved in diethyl ether, heptane was added, and the mixture was stirred overnight. Solvent was removed by syringe to give product as a pale brown solid, 27 mmol, 80%.

Workup

  1. extractionextracted with dichloromethane (5×200 mL)
  2. dry with materialThe organics were dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto give a brown solid
  5. customSolvent was removed by syringe
  6. customto give product as a pale brown solid, 27 mmol, 80%

Sources & evidence

ORD record
ord-7b8b7bbf03ae41a4b7fbb33233ce36a3
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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