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

HRID 1827969Notes

Reaction equation

HRID 1827969 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-355cc442d32f4968a61173645c593107
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

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