[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH2:2][CH3:3].[Br:12][CH2:13][CH2:14]Br.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:12][CH2:13][CH2:14][O:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[CH:6]=1A solution of 3-(n-propoxy)phenol (15.2 g; 0.1 mol; from Example A above) in 1,2-dibromoethane (100 ml; 1.16 mol) was added to a solution of tetrabutylammonium hydrogen sulphate (34 g; 0.1 mol) and sodium hydroxide (8.0 g; 0.2 mol) in water (100 ml). The mixture was stirred vigorously whilst a 50% solution of sodium hydroxide in water (33 ml) was added dropwise over half an hour. Stirring was subsequently continued for one hour. The organic phase was separated, washed with water and dried over magnesium sulphate. The solvent was evaporated and the residue treated with diethyl ether (150 ml). The precipitated salt was removed by filtration and the diethyl ether evaporated. The residue was distilled to yield (14.0 g; 54%) of the title compound as an oil (97% purity). bp 112-115° C. (0.05 mm Hg) MW=259 (GC-MS)
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