Benzene → 4,4-Dimethylthiochroman

반응식

C1([CH:7]([S:12]C(C2C=CC=CC=2)C=C(C)C)[CH:8]=[C:9]([CH3:11])[CH3:10])C=CC=CC=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(=O)(O)(O)O.[CH:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH3:10][C:9]1([CH3:11])[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[S:12][CH2:7][CH2:8]1

참가 물질

반응물 4

HCID 241Benzene

HCID 1004Phosphoric Acid

HCID 14812Phosphorus oxide (P4O10)

HCID 54518102Phenyl-3-methylbut-2-enylsulfide

생성물 1

HCID 110194304,4-Dimethylthiochroman

실험 절차

To a solution of 15.48 g (86.824 mmol) of phenyl-3-methylbut-2-enylsulfide (from Example 1) in 160 ml benzene were added successively 12.6 g (88.767 mmol) of phosphorus pentoxide and 11 ml of 85% phosphoric acid. This solution was refluxed with vigorous stirring under argon for 20 hours, then cooled to room temperature. The supernatant organic layer was decanted and the syrupy residue extracted with 3×50 ml ether. Organic fractions were combined and washed with water, saturated NaHCO3 and saturated NaCl solutions and then dried (MgSO4). Solvent was removed in vacuo and the residue purified by kugelrohr distillation (80° C., 0.5 mm) to give the title compound as a pale yellow oil. PMR (CDCl3) :δ 1.30 (6H, s), 1.90-1.95 (2H, m), 2.95-3.00 (2H, m), 6.96-7.00 (2H, m), 7.04-7.07 (1H, m), 7.30-7.33 (1H, m).