HEXANOIC-D11 ACID synthesis

Yield:95348-44-0 75%

Reaction Conditions:

with [D]-sodium hydroxide;10% Pt/activated carbon;water-d2 at 220; for 144 h;

Steps:

n-Hexanoic acid-d₁₁ (3)

General procedure: A mixture of hexanoic acid (13 g, 111.99 mmol), 0.6 g of Pt/C (10 wt % of the substrate) and NaOD (4.6 g, 111.99 mmol, 40% in D₂O) in D₂O (120 mL) was stirred under hydrothermal conditions for 2 cycles each 3 days at 220 °C in a Parr pressure reactor (600 mL size). After cooling, the reaction mixture was diluted with dichloromethane (200 mL) and the mixture was filtered through Celite to remove the catalyst. The filtered catalyst was washed with water and the filtrate acidified to pH 2. The aqueous phase was extracted with diethyl ether (100 mL × 3) and the combined organic phases were dried over Na₂SO₄, filtered and concentrated in vacuo to give oily substance 3 (10.7 g, 75% yield, 97% D ±2). ²H NMR (102.6 MHz, CDCl₃) _δD 2.31 (2.00 D, br s), 1.59 (2.04 D, br s), 1.27 (4.06 D, br s) 0.85 (3.03 D, br s). Isotope distribution (ESI-MS, -ve mode): 69% d₁₁, 31% d₁₀. (Figures S1-S2)

References:

Yepuri, Nageshwar R.;Jamieson, Scott A.;Darwish, Tamim A.;Rawal, Aditya;Hook, James M.;Thordarson, Pall;Holden, Peter J.;James, Michael [Tetrahedron Letters,2013,vol. 54,# 20,p. 2538 - 2541] Location in patent:supporting information