2-Phenylbenzofuran-7-carboxylic acid → 2-Cyclohexylbenzofuran-7-carboxylic acid

HRID 1761906

Reaction equation

HRID 1761906 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.O1CCCC1.[Pt]=O>[CH:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 142297062-Phenylbenzofuran-7-carboxylic acid

Product 1

HCID 142297092-Cyclohexylbenzofuran-7-carboxylic acidYield 60.1%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.5 g of 2-phenylbenzofuran-7-carboxylic acid is dissolved in a mixture of 80 ml of methanol and 16 ml of tetrahydrofuran and 0.5 g of platinum oxide is added to the solution. The mixture is subjected to catalytic hydrogenation under atmospheric pressure. The reaction mixture is filtered and the filtrate is evaporated to remove solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=20:1) to give 1.54 g of 2-cyclohexylbenzofuran-7-carboxylic acid as colorless oil.

Workup

  1. additionis added to the solution
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate is evaporated
  4. customto remove solvent
  5. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-6e53bd05d1db455ca47f8363c774f39f
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Linked notes

Loading…