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

HRID 970791Notes

Reaction equation

HRID 970791 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>[OH:16][CH2:15][C:13]1[O:14][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:18][C:11]=2[CH:12]=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 16 (2.1 g, 8.8 mmole) dissolved in THF (50 ml) was cooled to 5° C. in an ice bath, and LiAlH4 (0.67 g, 17.6 mmole) 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 2-hydroxymethyl-5-phenyl-benzofuran 17, 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-64e530677ec14a9ca7619693f39dcf94
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

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