4-Methylbenzoyl Chloride → Methyl 2-(4-Methylbenzoyl)-4,5-methylenedioxyphenylacetate

HRID 442658Notes

Reaction equation

HRID 442658 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.[C:15]1([CH3:24])[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][CH:16]=1>C(Cl)Cl.Cl[Sn](Cl)(Cl)Cl>[CH3:24][C:15]1[CH:20]=[CH:19][C:18]([C:21]([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:22])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetate

Product 1

HCID 10710218Methyl 2-(4-Methylbenzoyl)-4,5-methylenedioxyphenylacetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24287Tin tetrachlorideSolvent

Procedure

The title compound was prepared from methyl 3,4-methylenedioxyphenylacetate (319 mg, 1.64 mmol) in CH2Cl2 (5 mL), SnCl4 (1.0M solution in CH2Cl2 ; 3.5 mL mmol) and 4-toluoyl chloride (260 μL, 1.97 mmol) as an oily solid (90 mg, 18%). 1H NMR (CDCl3) 7.69 (d, 2H, J=8.0), 7.24 (d, 2H, J=8.0), 6.88 (s, 1H), 6.83 (s, (s, 2H), 3.78 (s, 2H), 3.60 (s, 3H), 2.43 (s, 3H).

Sources & evidence

ORD record
ord-7b5b635c632d4fbd8c5bd5e452170df8
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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