Water → HCID 86607742, compound

HRID 418872Notes

Reaction equation

HRID 418872 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:15]([C:16](=[O:18])[CH:17]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.[CH3:19][C:20]([O:22]C(C)=O)=[O:21].CCN(CC)CC.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:18]=[C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH2:19][C:20]([OH:22])=[O:21])=[CH:3][CH:4]=2)=[CH:17]1.[C:20]([OH:22])(=[O:21])[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 2290162H-1-BENZOPYRAN-2-ONE, 2-(4-HYDROXYPHENYL)-

Product 1

HCID 86607742HCID 86607742, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer were placed 2-(4-hydroxyphenyl)chromen-4-one (150 mg, 0.63 mmol), Ac2O (96 mg, 0.94 mmol), Et3N (96 mg, 0.94 mmol) and catalytic amount of DMAP in DCM (2 mL) and then the reaction mixture was stirred for 24 h at rt. The reaction mixture was poured into water and extracted with EtOAc. The organic layer washed with water, dried and concentrated to gave 160 mg of acetic acid 4-(4-oxo-4H-chromen-2-yl)phenyl acetate (91%). MS (ES) m/z: 281.15 (M+1), and 239.12.

Workup

  1. customIn a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer
  2. extractionextracted with EtOAc
  3. washThe organic layer washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54ac98132f5a42b6ae6ffaef12e5c493
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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