Water → HCID 18984733, compound

To a solution of 2-(3-hydroxypropyl)-4-chloro-toluene (6.2 g, 33.5 mmol) and triethylamine (9.34 mL, 67 mmol) in dichloromethane (25 mL) was added acetic anhydride (5.1 mL, 50.3 mmol) at room temperature. The mixture was stirred for 2 h and concentrated in vacuo. The residue was diluted with aq. KHSO4 and extracted with AcOEt. The extracts were dried and concentrated. The residue was dissolved in dichloromethane (50 mL). NO2 +BF4- (5.77 g, 36.85 mmol) was added at 0° C. The mixture was stirred for 30 min at 0° C. and poured into water. The mixture was extracted with AcOEt and the extracts was dried and concentrated. The residue was purified by silica gel column chromatography with 5:1 hexane/AcOEt to give 5.0 g of the title compound: 1H NMR (CDCl3) δ7.63 (bs, 1H), 7.36 (bs, 1H), 4.13 (t, 2H, J=7.2 Hz), 2.78 (t, 2H, J=7.2 Hz), 2.41 (s, 3H), 2.09 (s, 3H), 1.89~2.01 (m, 2H).

1. concentrationconcentrated in vacuo
2. additionThe residue was diluted with aq. KHSO4
3. extractionextracted with AcOEt
4. customThe extracts were dried
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in dichloromethane (50 mL)
7. stirringThe mixture was stirred for 30 min at 0° C.
8. extractionThe mixture was extracted with AcOEt
9. customthe extracts was dried
10. concentrationconcentrated
11. customThe residue was purified by silica gel column chromatography with 5:1 hexane/AcOEt

ORD record

ord-0e746d1210894787b6b9018e0d451a0f

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05496843