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

HRID 2120581Notes

Reaction equation

HRID 2120581 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
50 °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 50° 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-76c9e231e4e84ce1a0b567c456a1024b
Source dataset
uspto-grants-2004_02
Patent number
US06693098B2

Reaction notes

Loading…