Acetic Anhydride → N-[(2-Hydroxyphenyl)methyl]acetamide

Temperature

0 °C

2-Methoxybenzylamine (822 mg, 6.0 mmol) in methanol (10 mL) was treated with acetic anhydride (613 mg, 6.0 mmol) at room temperature for 2 h. The volatiles were removed in vacuo. The residue was dissolved in CH2Cl2, cooled to 0° C., 1M solution of BBr3 in CH2Cl2 (12 mL, 12.0 mml) was added slowly. After addition was completed the reaction mixture was stirred at room temperature overnight, cooled to 0° C., methanol (3 mL) was added and after 10 min volatiles were removed in vacuo. The residue was dissolved in ethyl acetate, washed successively with aqueous NaHCO3 and H2O. The organic layer was dried over Na2SO4 filtered and concentrated. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum spirit) to give the subtitled compound (400 mg).

1. customThe volatiles were removed in vacuo
2. dissolutionThe residue was dissolved in CH2Cl2
3. addition1M solution of BBr3 in CH2Cl2 (12 mL, 12.0 mml) was added slowly
4. additionAfter addition
5. temperaturecooled to 0° C.
6. additionmethanol (3 mL) was added and after 10 min volatiles
7. customwere removed in vacuo
8. dissolutionThe residue was dissolved in ethyl acetate
9. washwashed successively with aqueous NaHCO3 and H2O
10. dry with materialThe organic layer was dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated
13. customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum spirit)

ORD record

ord-e72c213d05474d4890d4901341c88629

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07498338B2