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ChemicalBook CAS DataBase List 2-Methyl-2-propyl-1,3-propanediol

2-Methyl-2-propyl-1,3-propanediol synthesis

4synthesis methods
-

Yield:-

Reaction Conditions:

Stage #1: methylpropylpropanedioic acid diethyl esterwith lithium aluminium tetrahydride in tetrahydrofuran at 20; for 2 h;
Stage #2: with water in tetrahydrofuran;

Steps:

1.2

Step 2; 2-Methyl-2-propylpropane-1,3-diol: Diethyl 2-methyl-2-propylmalonate (28 g, 116.67 mmol, 1.00 equiv) was added to a suspension of lithium aluminum hydride (12.3 g, 323.68 mmol, 2.77 equiv) in tetrahyrdofuran (200 mL). The resulting mixture was maintained at ambient temperature for about 2 hours, and then water (200 mL) was added. Following standard extractive workup with ethyl acetate, the crude product was purified by crystallization from ethyl acetate/hexane (1:10) to give the title product as white solid (12.0 g, 90.91 mmol). 1H NMR (300 MHz, CDCl3) δ: 3.60 (dd, J=10.8, 10.5 Hz, 4H), 2.24 (s, 2H), 1.33 (m, 4H), 0.95 (t, J=2.7, 3.3 Hz, 3H), 0.86 (s, 3H).

References:

US2010/76074,2010,A1 Location in patent:Page/Page column 10

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