Hydrochloric Acid → 2-(2-Hydroxy-5-methoxyphenyl)-4-methoxyphenol

Participants

Reaction Conditions

Reaction Steps

Part A: 2,2'-dihydroxy-5,5'-dimethyoxy-1,1'-biphenyl was prepared by the dealkylation of 2,2'-dihydroxy-3,3'-di-t-butyl-5,5'-dimethyoxy-1,1'-biphenyl using a procedure described by Tashiro, M.; Fukata, G., and Yamato, T.; Organic Preparations and Procedures Int., 8, 263 (1976). AlCl3 (10 g) and 10 g of 2,2'-dihydroxy-3,3'-di-t-butyl-5,5'-dimethoxy-1,1'-biphenyl were mixed in 125 ml of benzene and heated at 40° C. for 3 h. The mixture was cooled in ice and 125 ml of 10% HCl solution was added slowly. The organic layer was separated and washed with 3×125 ml of 10% NaOH. The basic solution was neutralized with concentrated HCl and extracted with 3×100 ml of ether. The ether layer was dried over Na2SO4. After filtering and removing the solvent by vacuum evaporation, the brown oil was washed with hexane and then the product crystallized from CH2Cl2 /hexane. 2.202 g of 2,2'-dihydroxyl-5,5'-dimethoxy-1,1'-biphenyl was obtained as a white solid. 1H nmr (300 MHz, CD2Cl2): 6.9-6.8 (m, 6H), 5.71 (s, 2H), 3.78 (s, 6H).

Provenance & Evidence