Benzyl Chloride → Benzyl 4-Benzyloxyphenyl Ketone

Benzyl 4-hydroxyphenyl ketone (5.1 g; 24 mmol), 3.8 g (3.5 mL, 30 mmol) of benzyl chloride, and 16.6 g (120 mmol) of pulverized and flame dried K2CO3 were slurried in 75 mL dry Me2CO under Ar. The mixture was heated to reflux 16 h, cooled to room temperature, diluted with CH2Cl2 (100 mL), and filtered. The resulting filter cake was washed with C6H6 (50 mL) and EtOAc (50 mL). The combined filtrates were concentrated and the resulting orange oil was dissolved in C6H6, washed with 10% K2CO3 (100 mL), 5% NaOH (2×50 mL), and H2O (100 mL). The organic layer was dried (MgSO4), filtered, and concentrated to give 10 g of a light orange solid, which was purified on 60 g flash SiO2 (1:1 petroleum ether-CH2Cl 2) to give Benzyl 4-benzyloxphenyl ketone as a clear oil which was crystallized from C6H6 -EtOH to yield 3.1 g of white needles (43%). mp: 134.5°-136° C. NMR δ 8.03 and 7.03 (AA'BB', c, 4H, ArH), 7.43 (s, 5H, ArH), 7.31 (s, 5H, ArH), 5.15 (s, 2H, PhCH2O), 4.25 (s, 2H, COCH2).

1. customdry Me2CO under Ar
2. temperatureThe mixture was heated
3. temperatureto reflux 16 h
4. additiondiluted with CH2Cl2 (100 mL)
5. filtrationfiltered
6. filtrationThe resulting filter cake
7. washwas washed with C6H6 (50 mL) and EtOAc (50 mL)
8. concentrationThe combined filtrates were concentrated
9. dissolutionthe resulting orange oil was dissolved in C6H6
10. washwashed with 10% K2CO3 (100 mL), 5% NaOH (2×50 mL), and H2O (100 mL)
11. dry with materialThe organic layer was dried (MgSO4)
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-af1dd27e9ebc48dba82e43e56f200860

Source dataset

uspto-grants-1991_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05015666