Hydrochloric Acid → 1-(3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one

To a stirred solution of acetyl chloride (4.78 mL, 67.1 mmol) in dry CH2Cl2 (20 mL) in a −10° C. bath is added aluminum trichloride (4.76 g, 35.7 mmol) in small portions. The mixture is stirred for 15 min until the solution became homogeneous. The solution is added via canula to a separate solution of chromane (4,79 g, 35.7 mmol) in CH2Cl2 (30 mL) all at −10° C. After complete addition, the solution is stirred at −10° C. for 30 min. The solution is poured over a mixture of crushed ice and concentrated HCl. The mixture is extracted with CH2Cl2. The combined organic layers are washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The remaining residue is purified via crystallization from hexanes to give 4.0 g (64%) of 1-(3,4-dihydro-2H-chromen-6-yl)ethanone as a white solid. 1H NMR (400 MHz, CDCl3) δ7.76-7.73, 6.75, 4.27, 2.86, 2.57, 2.09-2.03.

1. additionAfter complete addition
2. stirringthe solution is stirred at −10° C. for 30 min
3. extractionThe mixture is extracted with CH2Cl2
4. washThe combined organic layers are washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe remaining residue is purified via crystallization from hexanes

ORD record

ord-026f8d7314af4461b22dad7ebdf86d1a

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06951868B2