4-Fluorophenol → HCID 54066592, compound

A mixture of 4-fluorophenol (41.3 g, 0.37 M), 4-fluorobenzaldehyde (45.7 g, 0.37 M) and K2CO3 (55 g) in 450 mL DMF was refluxed for 4 h, cooled, poured into ice water (1.5 L) to give a suspension. The mixture was filtered, washed with water, dried at 50° C. under vacuum to generate 78.3 g of the aldehyde 20 as a brownish solid. This compound was slurried in 2-propanol (1 L), then NaBH4 (14 g, 0.378 M) was added portionwise at room temperature. The resulting mixture was stirred at room temperature for 1 h, then concentrated. The residue was poured into water (1.5 L) to give a suspension. After filtration, the resulting solid, washed with water, dried at 50° C. under vacuum to give 76 g of 4-fluorophenoxybenzyl alcohol 26 as a yellowish crystal.

1. temperaturewas refluxed for 4 h
2. temperaturecooled
3. customto give a suspension
4. filtrationThe mixture was filtered
5. washwashed with water
6. customdried at 50° C. under vacuum
7. additionNaBH4 (14 g, 0.378 M) was added portionwise at room temperature
8. concentrationconcentrated
9. additionThe residue was poured into water (1.5 L)
10. customto give a suspension
11. filtrationAfter filtration
12. washthe resulting solid, washed with water
13. customdried at 50° C. under vacuum

ORD record

ord-5a36f1be19474249a278c4d90cdb1cbd

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772237B2