2-METHYL DECANOL-2 synthesis
- Product Name:2-METHYL DECANOL-2
- CAS Number:3396-02-9
- Molecular formula:C11H24O
- Molecular Weight:172.31
Yield:3396-02-9 93%
Reaction Conditions:
with magnesium in diethyl ether at 25; for 48 h;Inert atmosphere;Grignard Reaction;
Steps:
Grignard-Type Phase-Vanishing Alkylation of Carbonyl Compounds;Typical Procedure (Table 1, entry 1):
GaldenHT135/200 = 1:1 (2 mL) was placed in a test tube(13 mm Φ × 105 mm), to which MeI (571 mg, 4.0 mmol) wasadded slowly using a glass pipette under argon. Anhydrous Et2O(1 mL) was added slowly, whereupon three layers formed. Mgpowder (98 mg, 4.0 mmol) was then added slowly, and floatedbetween the Galden and ether layers, whereupon four layersformed. Subsequently, a solution of 2-decanone (1a, 313 mg, 2.0mmol) in anhydrous Et2O (3 mL) was added to the ether layer.The bottom layer was stirred slowly at 25 °C for 2 d, taking carenot to mix the four layers. The ether solution and Mg salt weretaken into a flask, to which hydrochloric acid (2 M) was addedto quench the reaction, while cooling in an ice bath. The organiclayer was separated, and the aqueous layer was extracted withEt2O. The organic layer was collected, dried over Na2SO4, andconcentrated. The residue was purified by column chromatographyon silica gel (hexane-Et2O, 3:1) to give 2-methyl-2-decanol (2a)13 (320 mg, 93%) as a colorless oil; 1H NMR (500MHz, CDCl3): δ = 1.47-1.43 (m, 2 H, C-CH2), 1.34-1.28 (m, 12 H,alkyl), 1.21 (s, 6 H, 2 × C-CH3), 0.88 (t, J = 7.1 Hz, 3 H, CH2-CH3);13C NMR (126 MHz, CDCl3): δ = 70.97, 43.95, 31.81, 30.12, 29.53,29.20, 29.13, 24.28, 22.58, 14.01.
References:
Matsubara, Hiroshi;Niwa, Yuki;Matake, Ryosuke [Synlett,2015,vol. 26,# 9,p. 1276 - 1280]
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