Phthalaldehyde → HCID 10013151, compound

HRID 1648180Notes

Reaction equation

HRID 1648180 reaction equation
[CH:1](=[O:10])[C:2]1[C:3](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH:4]=O.[CH2:11]([O:13][C:14]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:15])[CH3:12]>ClCCl>[CH2:11]([O:13][C:14](=[O:15])/[CH:16]=[CH:4]/[C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[CH:1]=[O:10])[CH3:12]

Participants

4

Reactant 2

HCID 4807PhthalaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 10013151HCID 10013151, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of phthalaldehyde (6.7 g) in dichloromethane (30 ml) was added ethoxycarbonylmethylenetriphenylphosphorane (17.42 g) and the mixture was stirred for 30 minutes at room temperature. The solvent was evaporated and the residue was dissolved in diethyl ether. After the mixture was filtered, the filtrate was evaporated. The residue was distilled under vacuum (125° C., 0.6 mmHg) to give (E)-3-(2-formylphenyl)propenoic acid ethyl ester (6 g).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in diethyl ether
  3. filtrationAfter the mixture was filtered
  4. customthe filtrate was evaporated
  5. distillationThe residue was distilled under vacuum (125° C., 0.6 mmHg)

Sources & evidence

ORD record
ord-c4e78b6e76704b40b2a1d49483f3563d
Source dataset
uspto-grants-1995_07
Patent number
US05436140

Reaction notes

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