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

HRID 485180Notes

Reaction equation

HRID 485180 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:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)C>[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:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)[C:7]=2[CH:8]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 121745614-Hydroxy-2-methylbenzofuran

Product 1

HCID 13092105Ethyl 4-(2-methyl-4-benzofuranyloxymethyl)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Hydroxy-2-methylbenzofuran (7.4 g, 0.05 M), ethyl 4-bromomethylbenzoate (12.15 g, 0.05 M), anhydrous potassium carbonate (7.59 g), sodium iodide (0.3 g), and 95% ethanol were reacted together in an analogous manner to that described in example 5(A) to give ethyl 4-(2-methyl-4-benzofuranyloxymethyl)benzoate which was recrystallised from ethanol/water, m.p. 59°-61° C. (Found: C, 73.73; H, 6.03. C19H18O4 requires C, 73.55; H, 5.81%).

Sources & evidence

ORD record
ord-2e3debbdc55046b5bf4f75a0b5455dfa
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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