Hydrochloric Acid → 2-Hydroxymethyl-5-phenyl-benzofuran

HRID 1070385Notes

Reaction equation

HRID 1070385 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([C:15](O)=[O:16])=[CH:12][C:11]=3[CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C1COCC1>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([CH2:15][OH:16])=[CH:12][C:11]=3[CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 129909085-Phenyl-2-benzofurancarboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 113790942-Hydroxymethyl-5-phenyl-benzofuranYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 5-phenyl-benzofuran-2-carboxylic acid (2.1 g, 8.8 mmol) dissolved in THF (50 mL) was cooled to 5° C. in an ice bath, and LiAlH4 (0.67 g, 17.6 mmol) was added portionwise and stirred at room temperature for 1.5 hrs. The excess reagent was decomposed with an addition of 1M HCl, and the acidified mixture was extracted with ethyl acetate, washed, dried, and evaporated. The residue was purified by chromatography to give about 1.22 g of (5-phenyl-benzofuran-2-yl)-methanol, mp. 134-135° C.

Workup

  1. extractionthe acidified mixture was extracted with ethyl acetate
  2. washwashed
  3. customdried
  4. customevaporated
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-a76b3e4775a24719b064a5291621e5e7
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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