Sodium Iodide → Ethyl 6-(4-benzofuranyloxy)-hexanoate

HRID 485169Notes

Reaction equation

HRID 485169 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][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].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][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]=2[CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 117544Ethyl 6-bromohexanoateHCID 116079214-Benzofuranol

Product 1

HCID 20271555Ethyl 6-(4-benzofuranyloxy)-hexanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Hydroxybenzofuran (1.3 g, 0.0097 M), ethyl 6-bromohexanoate (2.17 g, 0.0097 M), anhydrous potassium carbonate (1.44 g), sodium iodide (60 mg) and 95% ethanol (10 ml) were reacted together to give ethyl 6-(4-benzofuranyloxy)-hexanoate which was subsequently hydrolysed, as previously described for the preparation of 5-(4-benzofuranyloxy)pentanoic awcid, to give 6-(4-benzofuranyloxy)hexanoic acid, m.p. 86°-87° C. (Found: C, 67.54; H. 6.48. C14H16O4 requires C, 67.73; H. 6.50%).

Sources & evidence

ORD record
ord-303a1ba73fbb4a49b876fbff65873977
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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