2-Chloro-4-nitrobenzoic acid → Methyl 2-(2-Chloro-4-nitrobenzoyl)-4,5-methylenedioxyphenylacetate

HRID 442683Notes

Reaction equation

HRID 442683 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:15][C:16]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:17]=1[C:18](O)=[O:19].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(Cl)CCl>[Cl:15][C:16]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:17]=1[C:18]([C:6]1[CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]2=[CH:4][C:5]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:19]

Participants

5

Reactant 3

HCID 74482-Chloro-4-nitrobenzoic acidHCID 14812Phosphorus oxide (P4O10)HCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetate

Product 1

HCID 54561972Methyl 2-(2-Chloro-4-nitrobenzoyl)-4,5-methylenedioxyphenylacetate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title compound was prepared from methyl 3,4-methylenedioxyphenylacetate (12.5 g, 64.4 mmol) in ClCH2CH2Cl (150 mL), 2-chloro-4-nitrobenzoic acid (25.0 g, 124 mmol) and P2O5 (37 g) as a yellow solid (11 g, 29 mmol, 45%). 1H NMR (CDCl3) 8.15 (s, 1H), 8.14 (d, J=8.4, 1H), 7.58 (d, J=8.4, 1H), 6.84 (s, 1H), 6.71 (s, 1H), 6.05 (s, 2H), 4.03 (s, 2H), 3.73 (s, 3H).

Sources & evidence

ORD record
ord-6d8cb946cb9747c18dbcd3ca89bd3c5c
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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