p-Anisoyl chloride → Methyl 2-(4-Methoxybenzoyl)-4,5-methylenedioxyphenylacetate

HRID 442659Notes

Reaction equation

HRID 442659 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=2[O:2]1.Cl[Sn](Cl)(Cl)Cl.[C:20](Cl)(=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]([C:6]2[CH:7]=[C:8]3[O:9][CH2:1][O:2][C:3]3=[CH:4][C:5]=2[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:29])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 24287Tin tetrachlorideHCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetate

Product 1

HCID 10735027Methyl 2-(4-Methoxybenzoyl)-4,5-methylenedioxyphenylacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from methyl 3,4-methylenedioxyphenylacetate (244 mg, 1.26 mmol) in CH2Cl2 (5 mL), SnCl4 (1.0M solution in CH2Cl2 ; 2.5 mL 2.5 mmol) and 4-anisoyl chloride (220 μL, 1.62 mmol) as a white solid (110 mg, 27%). 1H NMR (CDCl3) 7.78 (d, 2H, J=8.6), 6.93 (d, 2H, J=8.6), 6.86 (s, 1H), 6.83 (s, 1H), 6.03 (s, 2H), 3.88 (s, 3H), 3.75 (s, 2H), 3.59 (s, 3H).

Sources & evidence

ORD record
ord-000364a43b5641a4865807beb0d31316
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

Loading…