[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[OH-:19].[K+]>O>[OH:2][C:1]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[O:5][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:19][C:4]1[CH:6]=[CH:7][CH:8]=[C:1]([OH:2])[CH:3]=1A five neck five liter round bottom flask equipped with a mechanical stirrer, two condensers, and a dropping funnel was purged with nitrogen then charged under a nitrogen blanket with 1.6 kg (14.5 moles) resorcinol, 160 grams deionized water, and 296.7 grams (1.091 moles) 1,8-dibromooctane. The easily stirable reaction mass was slowly heated to reflux under a slow nitrogen purge. A solution of 181 grams (2.74 moles) 85 percent KOH pellets in 184 grams water was added dropwise at reflux under a nitrogen blanket over a period of two hours. After about 25 percent of the KOH had been added, the reaction mass had dissolved to light tea colored solution then it becomes increasingly clouded as salt was formed. The reaction mixture was refluxed an additional hour after all the KOH had been added. The pH of the reaction mixture was basic. The reaction was quenched with 1.5 liters of water and acidified with 40 percent sulfuric acid. The reaction mixture was then poured into 4 liters of water, cooled in an ice bath to a temperature of 10° C. and filtered to recover a tan colored solid which was slurried in 1.2 liters boiling water to wash out resorcinol and KBr. The cooled slurry was then filtered and 350 grams of crude product was recovered. Crystallization from 400 ml acetone yield 170 grams white crystals, 88 percent pure by HPLC peak area, and recrystallization from 500 ml acetone yields 97.4 grams product of 96 percent purity by HPLC peak area and high purity by gel permeation chromatography (m.p. 78°-82° C.).
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