Hydrochloric Acid → 4-{4-[(4-Bromobutyl)oxy]butyl}benzoic acid
Reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[CH:13][CH:12]=1.Cl.O1CCOCC1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:23]=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1Participants
4
Procedure
1,1-Dimethylethyl 4-{4-[(4-bromobutyl)oxy]butyl}benzoate (1.05 g, 2.72 mmol, e.g. which can be as prepared in Intermediate 24) was treated with a 4M solution of HCl in 1,4-dioxane (10 ml, 40 mmol, 15 equivalents) and the mixture was allowed to stand at room temperature overnight (about 16 hours). The solvent was evaporated in vacuo followed by several co-evaporations with dichloromethane and a trituration with diethyl ether (the material failed to solidify). The diethyl ether was evaporated off to give the title compound as greenish gum (0.91 g; product contained diethyl ether by NMR). LCMS showed MH+=329/331 (Bromine isotope pattern); TRET=3.60 min.