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

HRID 413687Notes

Reaction equation

HRID 413687 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 1, 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-206fc7957d8a430fbc1593235b1dec41
Source dataset
uspto-grants-2003_05
Patent number
US06569860B2

Reaction notes

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