Hydrochloric Acid → Bis(2-chlorophenyl)methanol

Temperature

-12.5 °C

Under N2, 1-chloro-2-iodobenzene (40 ml, 0.33 mol) was dissolved in THF (360 ml) and cooled to −10 to −15° C. Within 30 min, a 1M solution of ethyl magnesium bromide (344 ml, 0.34 mol) in TBME was added at this temperature. The mixture was stirred at −10 to −15° C. and the reaction was followed by HPLC. After the reaction was complete (15 to 30 min), a solution of 2-chloro benzaldehyde (40.7 ml, 0.36 mol) in TBME (160 ml) was added at −10 to −15° C. within 30 min and the reaction was followed by HPLC. After complete reaction (15 to 30 min), the mixture was hydrolized with dilute HCl until all solids were dissolved at a final temperature of 20 to 25° C. The organic phase was washed with water (2×40 ml) and evaporated to dryness at a temperature of 45 to 50° C. The residue was co-evaporated twice with heptane (80 ml each) and crystallized from hot n-heptane (280 ml at 95 to 100° C.). The product was isolated by filtration after stirring for 1 h at 0 to 5° C. and washed with cold n-heptane (40 ml at 0 to 5° C.). The product was dried under vacuum at 50° C. to constant weight. Yield: 73.4 g (88%). Assay (HPLC): 100% pure vs. standard.

1. custom(15 to 30 min)
2. customAfter complete reaction (15 to 30 min)
3. dissolutionwere dissolved at a final temperature of 20 to 25° C
4. washThe organic phase was washed with water (2×40 ml)
5. customevaporated to dryness at a temperature of 45 to 50° C
6. customcrystallized from hot n-heptane (280 ml at 95 to 100° C.)
7. customThe product was isolated by filtration
8. stirringafter stirring for 1 h at 0 to 5° C.
9. washwashed with cold n-heptane (40 ml at 0 to 5° C.)
10. customThe product was dried under vacuum at 50° C. to constant weight

ORD record

ord-45de4ccb79914330b9716e97675f85b2

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07459556B2