Hydrochloric Acid → 1,8-Naphthalenedimethanol

Temperature

95 °C

A 12-L 4-neck flask equipped with a thermocouple, an overhead stirrer, a 2-L addition funnel, and a condenser under N2 was charged with 1,8-naphthalic anhydride (200 g, 1.0 mol) in toluene (2.5 L) at room temperature. The reaction mixture was agitated while adding DIBAL-H (1.5 M in toluene, 2.664 L, 4 mol) via the addition funnel over 1.5 h. The solution was then heated to 95° C. overnight, cooled to 15° C. and then slowly diluted with ethyl acetate (2.2 L) and H2O (2 L) followed by addition of concentrated HCl (320 mL). The resulting suspension was stirred for 30 min at room temperature, filtered, and air dried on the filter for 2 h. The resultant material was in 95% ethanol (1.2 L), stirred at 70° C. for 2 h, and filtered to yield a wet solid which was air dried overnight on the filter and then dried at 70° C. in a vacuum oven to yield (8-hydroxymethyl-naphthalen-1-yl)-methanol as a solid;

1. customA 12-L 4-neck flask equipped with a thermocouple, an overhead stirrer
2. temperaturecooled to 15° C.
3. stirringThe resulting suspension was stirred for 30 min at room temperature
4. filtrationfiltered
5. customair dried on the
6. filtrationfilter for 2 h
7. stirringstirred at 70° C. for 2 h
8. filtrationfiltered
9. customto yield a wet solid which
10. customdried overnight on the
11. filtrationfilter
12. customdried at 70° C. in a vacuum oven

ORD record

ord-0209447c49984b3d98376c24500a78c3

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582649B2