1,3-Benzodioxole-5-carboxylic acid → Methyl 2-(2-(3,4-Methylenedioxybenzoyl)-4,5-methylenedioxyphenyl)propionate

HRID 442678Notes

Reaction equation

HRID 442678 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.[C:16](O)(=[O:26])[C:17]1[CH:25]=[CH:24][C:23]2[O:22][CH2:21][O:20][C:19]=2[CH:18]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>ClCCCl>[CH2:21]1[O:22][C:23]2[CH:24]=[CH:25][C:17]([C:16]([C:6]3[CH:7]=[C:8]4[O:9][CH2:1][O:2][C:3]4=[CH:4][C:5]=3[CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[O:26])=[CH:18][C:19]=2[O:20]1

Participants

5

Reactant 3

HCID 71961,3-Benzodioxole-5-carboxylic acidHCID 14812Phosphorus oxide (P4O10)HCID 453581932-Benzo[1,3]dioxol-5-YL-propanoic acid methyl ester

Product 1

HCID 53977841Methyl 2-(2-(3,4-Methylenedioxybenzoyl)-4,5-methylenedioxyphenyl)propionate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of methyl 2-(3,4-methylenedioxyphenyl)propionate (1 g, 4.8 mmol) in 1,2-dichloroethane (50 mL) was added piperonylic acid (1.6 g, 9.6 mmol) and P2O5 (4 g). The reaction mixture was stirred for 15 h and then poured to ice water (200 mL) and the product was extracted with EtOAc (2×100 mL). The pure product was obtained by flash chromatography (453 mg, 27%). 1H NMR (CDCl3) 7.37 (s, 1H), 7.33 (d, J=8.0, 1H), 6.95 (s, 1H), 6.83 (d, J=8.0, 1H), 6.76 (s, 1H), 6.07 (s, 2H), 6.02 (s, 2H), 3.95 (q, J=7.1, 1H), 3.58 (s, 3H), 1.45 (d, J=7.1, 3H).

Workup

  1. extractionthe product was extracted with EtOAc (2×100 mL)
  2. customThe pure product was obtained by flash chromatography (453 mg, 27%)

Sources & evidence

ORD record
ord-ddf4f2dbe8b447f8a1d9b7e36a0ed293
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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