HCID 10108002, compound → HCID 11777139, compound

Participants

Reaction Steps

3,5-Dimethyl-4-(3'-isopropylphenoxy)-nitrobenzene (5.21 g) and 521 mg of 10% platinum on carbon in 150 ml ethanol are reduced under hydrogen on a Parr shaker. The solution is filtered through Celite to remove catalyst and the filtrate is stripped to give 3,5-dimethyl-4-(3'-isopropylphenoxy)-aniline which is then fused with 50 g of dimethyl oxalate at 120° for four hours. The resulting mixture is concentrated under high vacuum and the residue chromatographed on silica gel with 9:1 toluene:ethyl acetate as eluent to yield methyl N-[3,5-dimethyl-4-(3'-isopropylphenoxy)-phenyl]oxarnate; NMR (CDCl3): δ 5 1.2 (6H, d), 2.1 (6H,s), 2.8 (1H,m), 4.0 (3H,s), 6.5 (1H, d of d), 6.7 (1H,t), 6.9 (1H, d of d), 7.2 (1H, t), 7.4 (2H,s), 8.8 (1 h, br s).

Provenance & Evidence