Benzoyl chloride → Methyl 2-(2-Benzoyl-4,5-methylenedioxyphenyl)propionate

HRID 442674Notes

Reaction equation

[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=2[O:2]1.Cl[Sn](Cl)(Cl)Cl.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:21]([C:6]1[CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]2=[CH:4][C:5]=1[CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of methyl 2-(3,4-methylenedioxyphenyl)propionate (1.04 g, 5 mmol) in CH2Cl2 (30 mL) at 0° C. was added SnCl4 (1M solution in CH2Cl2, 9 mL, 9 mmol). Then a solution of benzoyl chloride (1 mL) in CH2Cl2 (10 mL) was added dropwise and the mixture obtained was warmed to 25° C. for 20 h with stirring. The reaction mixture was poured into a separatory funnel containing Na2CO3 solution (sat. 50 mL) and some ice. The organic layer was separated and the aqueous was extracted with CH2Cl2 (3×50 mL). The combined extracts were washed with water (50 mL), NaHCO3 (sat. 40 mL) and brine (50 mL) and dried over Na2SO4. The pure product (360 mg, 23%) was obtained by chromatography on silica gel (hexane/ethyl acetate=4:1). 1H NMR (CDCl3) 7.80-7.45 (m, 5H), 6.96 (s, 1H), 6.79 (s, 1H), 6.03 (s, 2H) 3.70 (m, 1H), 3.58 (s, 3H), 1.47 (d, J=7.4, 3H).

Workup

customthe mixture obtained
additionThe reaction mixture was poured into a separatory funnel
customThe organic layer was separated
extractionthe aqueous was extracted with CH2Cl2 (3×50 mL)
washThe combined extracts were washed with water (50 mL), NaHCO3 (sat. 40 mL) and brine (50 mL)
dry with materialdried over Na2SO4

Sources & evidence

ORD record: ord-c41a217b5bd2480f9c3f4b592864e9b2
Source dataset: uspto-grants-1999_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05891871

Reaction notes

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