Sodium Iodide → Methyl 2-(2-methyl-4-benzofuranyloxymethyl)benzoate

HRID 485172Notes

Reaction equation

HRID 485172 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.Br[CH2:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CO>[CH3:11][C:9]1[O:10][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([O:1][CH2:13][C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]([O:18][CH3:19])=[O:17])[C:7]=2[CH:8]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 121745614-Hydroxy-2-methylbenzofuran

Product 1

HCID 20271537Methyl 2-(2-methyl-4-benzofuranyloxymethyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Hydroxy-2-methylbenzofuran (2/3 g, 14.4 M), methyl 2-bromomethylbenzoate (3.29 g, 14.4 mM), anhydrous potassium carbonate (2.135 g), sodium iodide (87 mg) and methanol (20 ml) were reacted together in an analogous manner to that described in Example 5(A) to give methyl 2-(2-methyl-4-benzofuranyloxymethyl)benzoate, m.p. 93°-95° C. (Found: C, 72.74; H, 5.26. C18H16O4 required C, 72.96; H, 5.44%).

Sources & evidence

ORD record
ord-23dae454284c40999ba7325741f314c3
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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