Methyl 4-Formylbenzoate → HCID 86749511, compound

HRID 440828Notes

Reaction equation

HRID 440828 reaction equation
[Br-].[Cl:2][C:3]1[CH:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:25][C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[O-].[Na+].[CH:36]([C:38]1[CH:47]=[CH:46][C:41]([C:42]([O:44][CH3:45])=[O:43])=[CH:40][CH:39]=1)=O>O1CCCC1>[Cl:2][C:3]1[CH:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:25][C:4]=1/[CH:5]=[CH:36]\[C:38]1[CH:39]=[CH:40][C:41]([C:42]([O:44][CH3:45])=[O:43])=[CH:46][CH:47]=1

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 10942334Sodium MethoxideHCID 22404900HCID 22404900, compound

Product 1

HCID 86749511HCID 86749511, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 52.6 g of (2-chloro-4-methoxycarbonylbenzyl)-triphenylphosphonium bromide in 500 ml of tetrahydrofuran was treated at 0° C. with 115 ml of 2% methanolic sodium methylate solution. Then, a solution of 16.4 g of methyl 4-formylbenzoate was added dropwise within 10 minutes and the mixture was stirred at room temperature for 1 hour. The suspension was filtered over Dicalite and the filtrate was evaporated. The residue was chromatographed using ethyl acetate/hexane/methylene chloride and gave dimethyl (Z)-2-chlorostilbene-4,4'-dicarboxylate, MS: m/z 330 (M+), and dimethyl (E)-2-chlorostilbene-4,4'-dicarboxylate as colourless crystals, m.p. 134°-135° C., MS: m/z 330 (M+).

Workup

  1. filtrationThe suspension was filtered over Dicalite
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed

Sources & evidence

ORD record
ord-8e8bb4929ffd45f4a518e127fb2f317d
Source dataset
uspto-grants-1996_05
Patent number
US05521160

Reaction notes

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