4-Chlororesorcinol → HCID 58913503, compound

HRID 1296892Notes

Reaction equation

HRID 1296892 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9].[C:10]([CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH2:28][C:29]([OH:31])=O)[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])#[N:11].P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:38]N(C=O)C>>[Cl:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][C:3]=1[OH:9])[O:6][CH:38]=[C:28]([C:18]1[CH:19]=[CH:20][C:21]([O:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])=[C:16]([O:15][CH2:14][CH2:13][CH2:12][C:10]#[N:11])[CH:17]=1)[C:29]2=[O:31]

Participants

5

Reactant 4

HCID 17314-ChlororesorcinolHCID 6228DimethylformamideHCID 24819Phosphorus pentachlorideHCID 58913490HCID 58913490, compound

Product 1

HCID 58913503HCID 58913503, compoundYield 72.5%

Procedure

This compounds was synthesised in the same manner as described above. 4-Chlororesorcinol (0.48 g, 3.31 mmol), [3,4-Bis-(3-cyano-propoxy)-phenyl]-acetic acid (1 g, 3.31 mmol), BF3Et2O (8 ml), PCl5 (1.03 g, 4.97 mmol), DMF (8 ml and 12 ml). The precipitate formed was filtered and re-crystallized from methanol to give 4-[4-(6-Chloro-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-(3-cyano-propoxy)-phenoxy]-butyronitrile as a white solid (1.05 g, 72.5%); Rf 0.6 ethyl acetate/hexane (80/20)].

Workup

  1. customThis compounds was synthesised in the same manner
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. customre-crystallized from methanol

Sources & evidence

ORD record
ord-8d79d7b92e674ca28f109903144055a9
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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