6-(methylthio)-1-indanone

Main page (Russian)

Search in database (English)

Properties of substance:

6-(methylthio)-1-indanone

skc-file

Synonyms:

6-(methylthio)-2,3-dihydro-1H-inden-1-one

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C₁₀H₁₀OS

Molar/atomic mass: 178.254

Synthesis 1:

Reference: Heffner, R. J., & Joullie, M. M. Synthetic Routes to Ninhydrins. Preparation of Ninhydrin, 5-Methoxyninhydrin, and 5-(Methylthio)Ninhydrin / Synthetic Communications. - 1991. - Vol. 21, No. 21 pp. 2251 [doi: 10.1080/00397919108055457]

To a mechanically stirred solution of polyphosphoric acid (300 g) at 100 °C, under nitrogen atmosphere was added 4-(methylthio)dihydrocinnamic acid (3.0 g, 15.2 mmol). The reaction was allowed to proceed for 10 minutes, and then quenched by adding it to a methylene chloride-ice mixture (700 mL). The organic layer was separated and the aqueous layer extracted with methylene chloride (100 mL, 4x). The organic layers were combined and washed successively with 2.5% NaOH solution (100 mL), 2N HCl solution (100 mL), and water (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 6-(methylthio)-1-indanone (2.24 g, 82% yield), mp 105—108 °C.

R_f 0.44 petroleum ether : ethyl acetate (90 : 10).

HRMS calcd. for C10H10OS (M+): 178.0452. Found 178.0460.

IR (CHCl3): 3020 (medium), 2940 (medium), 1710 (strong), 1605 (medium), 1570 (weak), 1475 (medium), 1440 (medium), 1400 (medium), 1320 (medium), 1285 (medium), 1260 (medium), 1250 (medium), 1180 (medium), 1120 (medium), 1035 (weak), 970 (weak), 955 (weak), 860 (weak), 830 (medium) cm^-1.

1H NMR (CDCl3): δ 2.51 (3H, s), 2.71 (2H, m), 3.10 (2H, m), 7.38 (1H, d, J = 8.1 Hz), 7.49 (1H, dd, J₁ = 1.7 Hz, J₂ = 8.1 Hz), 7.57 (1H, s).

References:

Your requests if no data into database