4-(4-METHYLPHENOXY)PHENOL synthesis

7synthesis methods

Product Name:4-(4-METHYLPHENOXY)PHENOL
CAS Number:35094-91-8
Molecular formula:C13H12O2
Molecular Weight:200.23

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Yield:35094-91-8 95%

Reaction Conditions:

Stage #1: 1-methoxy-4-(p-tolyloxy)benzenewith boron tribromide in dichloromethane at 0 - 20;Inert atmosphere;
Stage #2: with water in dichloromethane;

Steps:

9.1.2

DemethylationUnder inert atmosphere, the methoxyether derivative previously prepared was dissolved in dichloromethane. The reaction mixture was cooled to 0° C. before adding a molar solution of boron tribromide in dichloromethane (2eq) drop by drop. The reaction mixture was stirred at 0° C. for 30 minutes, then at room temperature for 3 hours. The mixture was then partitioned between water and dichloromethane. The organic layer was washed with a sodium hydroxide 2N solution. The aqueous layer was acidified to pH 1 and extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, and evaporated under reduced pressure.9.1.2 4-(p-tolyloxy)phenol Prepared following the demethylation method previously described (Method 9A) using 1-methoxy-4-(p-tolyloxy)benzene (example 9.1.1). The product was obtained as a beige solid. Yield: 95% Rf (cyclohexane/ethyl acetate 8/2): 0.32 NMR ¹H (CDCl₃): 2.30 (s, 3H); 4.86 (s, 1H); 6.72-6.95 (m, 6H); 7.10 (d, 2H, J=8.2 Hz).

References:

US2010/4159,2010,A1 Location in patent:Page/Page column 55-56