ChemicalBook CAS DataBase List (R)-1-(3-Chlorophenyl)-2-hydroxy-1-propanone

(R)-1-(3-Chlorophenyl)-2-hydroxy-1-propanone synthesis

6synthesis methods

Product Name:(R)-1-(3-Chlorophenyl)-2-hydroxy-1-propanone
CAS Number:291275-46-2
Molecular formula:C9H9ClO2
Molecular Weight:184.62

1-Chloro-3-[(1Z)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propen-1-yl]-benzene

291275-45-1
2 suppliers
inquiry

(R)-1-(3-Chlorophenyl)-2-hydroxy-1-propanone

291275-46-2
7 suppliers
$150.50/50mg

Yield:291275-46-2 87%

Reaction Conditions:

with methanesulfonamide;1,4-bis(9-O-dihydroquinidine)phthalazine in water;tert-butyl alcohol at 0; for 16 h;

Steps:

2

Step 2: (i~)-l-(3-ChIorophenyl)-2-hydroxypropan-l-one ((/~)- 10a).; A mixture of AD-mix-β (50.6 g) and CH₃S0₂NH₂ (3.5 g, 0.037 mol) in fert-butyl alcohol-water (120 mL/120 mL) was cooled at 0 °C and treated with 9a (10 g, 0.036 mol). The reaction mixture was stirred for 16 h at 0 °C. Sodium sulfite (36 g) was added and the mixture was stirred for another hour. The mixture was filtered through a Celite pad and washed with ether. The filtrate was transferred to a separation funnel and the lower dark colored layer was discarded. The upper yellowish phase was separated, dried (Na₂S0₄), filtered, and concentrated. The crude product was purified by column chromatography on silica gel using hexanes-EtOAc (10: 1 to 3: 1) as the eluent to give 5.8 g (87%) of title product as light greenish oil: [a]²⁰_D +64.2° (c 1.2, CHC1₃); 1H NMR (CDC1₃) δ 7.91 (s, 1H), 7.80 (d, 1H, J = 7.8 Hz), 7.62-7.57 (m, 1H), 7.46 (t, 1H, J = 7.8 Hz), 5.15-5.08 (m, 1H), 3.68-3.65 (m, 1H), 1.45 (d, 3H, J - 7.1 Hz). C₉H iC10₂. Characterization data is similar to that reported in Fang, Q. K. et al, Tetrahedron: Asymmetry 2000, 11 : 3659-3663.