1,4-Dichlorobenzene → Ethyl 5-allyl-4-hydroxy-3-methylbenzofuran-2-carboxylate

HRID 978112Notes

Reaction equation

HRID 978112 reaction equation
C([O:4][C:5]1[C:10]2[C:11]([CH3:19])=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1)C=C.[CH:20]1[C:25](Cl)=CC=C(Cl)[CH:21]=1>>[CH2:25]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:11]([CH3:19])[C:10]=2[C:5]=1[OH:4])[CH:20]=[CH2:21]

Participants

3

Reactant 2

HCID 46851,4-DichlorobenzeneHCID 13849488Ethyl 4-allyloxy-3-methylbenzofuran-2-carboxylate

Product 1

HCID 13849523Ethyl 5-allyl-4-hydroxy-3-methylbenzofuran-2-carboxylateYield 85%

Procedure

A solution of ethyl 4-allyloxy-3-methylbenzofuran-2-carboxylate (1.04 g, 4 mmol, Example 116) in dichlorobenzene was refluxed for 3 hours. The resulting solution was chromatographed (silica gel, 5% ethyl acetate in hexane) to give 8.7 g of the title compound (85% yield), m.p. 123° C.

Workup

  1. customThe resulting solution was chromatographed (silica gel, 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9783708625d04cf3aece88f8b32303a7
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

Loading…