Sodium Iodide → Ethyl 4-(4-benzofuranyloxy)butanoate

HRID 485168Notes

Reaction equation

HRID 485168 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)C>[O:10]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([O:1][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7]=2[CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 116079214-Benzofuranol

Product 1

HCID 20271545Ethyl 4-(4-benzofuranyloxy)butanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Hydroxybenzofuran (1.0 g., 0.00746 M), ethyl 4-bromobutanoate (1.46 g, 0.00746 M), anhydrous potassium carbonate (1.13 g), sodium iodide (50 mg) and 95% ethanol (20 ml) were reacted together to give ethyl 4-(4-benzofuranyloxy)butanoate which was subsequently hydrolysed, as previously described for the preparation of 5-(4-benzofuranyloxy)pentanoic acid, to give 4-(4-benzofuranyloxy)butanoic acid, m.p. 91°-93° C. (Found: C, 65.50; H, 5.40. C12H12O4 requires C, 65.45; H, 5.45%).

Sources & evidence

ORD record
ord-7b148ef2d18b4a909b25917825fc4d7a
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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