Water → Methyl 4-((5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-YL)carbamoyl)benzoate

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Reaction Conditions

Reaction Steps

Terephthalic acid monomethyl ester (194 mg, 1.08 mmol) was dissolved in SOCl2 (5.39 mL) at 0° C. A drop of DMF was added and the mixture was stirred for 30 min. The SOCl2 was removed under vacuum and the crude acid chloride was dissolved in pyridine (12.5 mL). 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ylamine 6 (200 g, 0.98 mmol) and DMAP (12 mg, 0.1 mmol) was added and the mixture was heated at 60° C. for 2 h with stirring. The mixture was poured into H2O and the product was extracted with EtOAc. Them organic layer was washed successively with HCl 2M, saturated NaHCO3, saturated NaCl, dried over MgSO4 and filtrated to give after evaporation N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-terephthalamic acid methyl ester 7 (316 mg, 88% yield) as a white solid.

Provenance & Evidence