Diphenyl Ether → Ethyl 3-allyl-4-hydroxyphenoxyacetate
Reaction equation
C([O:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=1)C=C.[C:18]1(OC2C=CC=CC=2)[CH:23]=CC=C[CH:19]=1>>[CH2:23]([C:17]1[CH:16]=[C:8]([CH:7]=[CH:6][C:5]=1[OH:4])[O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:18]=[CH2:19]Participants
3
Procedure
A solution of ethyl 4-allyloxyphenoxyacetate (2.0 g) in diphenylether (15 ml) was heated at reflux for 12 minutes. The reaction mixture was allowed to cool to ambient temperature and the reaction mixture was poured onto a silica gel pad (Merck Art. No. 9385). Elution with hexane followed by a 4:1 (v/v) mixture of hexane and ethyl acetate gave ethyl 3-allyl-4-hydroxyphenoxyacetate (1.62 g) as a solid, mp 52.8° C.; microanalysis, found: C, 66.3; H, 7.20%; C13H16O4 requires: C, 66:1; H, 6.83%; NMR (CDCl3): 1.28 (3H, t), 3.35 (2H, d), 4.25 (2H, q), 4.55 (2H, s), 4.73 (1H, s), 5.07-5.20 (2H, m), 5.88-6.10 (1H, m) and 6.62-6.78 (3H, m); m/z 237 (M+H).
Workup
- temperatureat reflux for 12 minutes
- additionthe reaction mixture was poured onto a silica gel pad (Merck Art