Hydrochloric Acid → 4-Methoxy-2-(3',4',5'-tris(octadecyloxy)cyclohexylmethyloxy)benzyl alcohol

4-Methoxy-2-(3′,4′,5′-tris(octadecyloxy)cyclohexylmethyloxy)benzaldehyde (73.56 g, 69.8 mmol) was dissolved in THF-methanol (1100 ml+55 ml), and sodium borohydride (3.17 g, 83.8 mmol) was added at 0° C. After stirring the mixture at room temperature for 1.5 hr, 0.2N hydrochloric acid (150 ml) was added at 0° C. to quench the reaction. The solvent was evaporated to about half, and the residue was dissolved in chloroform (1400 ml), washed twice with 0.1N hydrochloric acid (700 ml), and twice with pure water (700 ml). The solvent was evaporated, and the residue was precipitated with methanol (800 ml), and washed with acetonitrile (800 ml) to give 4-methoxy-2-(3′,4′,5′-tris(octadecyloxy)cyclohexylmethyloxy)benzyl alcohol (71.5 g, 67.7 mmol, 92% vs methyl 3,4,5-tris(octadecyloxy)cyclohexylcarboxylate).

1. customto quench
2. customthe reaction
3. customThe solvent was evaporated to about half
4. dissolutionthe residue was dissolved in chloroform (1400 ml)
5. washwashed twice with 0.1N hydrochloric acid (700 ml)
6. customThe solvent was evaporated
7. customthe residue was precipitated with methanol (800 ml)
8. washwashed with acetonitrile (800 ml)

ORD record

ord-517881b28f2b46d9a7f1525b5aafc841

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859732B2