Chainlike Compounds are useful building blocks, especially in liquid crystal and medicinal chemistry.
Synthesis of Chainlike Compounds


To a stirred suspension of LAH (2.5 g, 0.066 mol) in ether (50 mL) was added the acid 1 (10.0 g, 0.055 mol) in ether (50 mL). The mixture was refluxed for 4 h and brought to room temperature, and the excess hydride was decomposed with aqueous saturated Na2SO4. The mixture was filtered and the solid residue washed with ether. The combined organic layer was concentrated in vacuo to yield 2 (7.8 g, 84%).


Hydrobromination of 1-decanol was performed in a 50 mL Schlenk flask using 10 mol% of DDAB. In a representative procedure, 1-decanol (10 mmol) was mixed with 10 mmol of hydrogen bromide in water and 3 mL of 30% hydrogen peroxide added. The whole system was stirred at 120 oC for 16 h. The yield is 100%.


To a cooled (0 °C) and stirred suspension of PCC (32.33 g, 0.15 mol) in CH2Cl2 (200 mL) was added 1(18.6 g, 0.1 mol) in one lot. After being stirred for 3 h, when the reaction was complete (cf. TLC), the reaction was quenched with anhydrous ether (200 mL). The mixture was stirred vigorously and the supernatant passed through a small pad (6 in.) of silica gel. The eluent was concentrated in vacuo to obtain 2 (16.56 g, 90%).


The application of Chainlike Compounds

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