4-Chlororesorcinol → HCID 58913601, compound

HRID 1296893Notes

Reaction equation

HRID 1296893 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][CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH2:23][C:24]([OH:26])=O)[CH:20]=[CH:21][CH:22]=1)#[N:11].P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:33]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:33]=[C:23]([C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][CH2:15][CH2:14][CH2:13][CH2:12][C:10]#[N:11])[C:24]2=[O:26]

Participants

5

Reactant 4

HCID 17314-ChlororesorcinolHCID 6228DimethylformamideHCID 24819Phosphorus pentachlorideHCID 58913632HCID 58913632, compound

Product 1

HCID 58913601HCID 58913601, compoundYield 59.1%

Procedure

This compound was synthesised in the same manner as described above. 4-Chlororesorcinol (0.37 g, 2.58 mmol), [3-(4-Cyano-butoxy)-phenyl]-acetic acid (0.6 g, 2.58 mmol), BF3Et2O (8 ml), PCl5 (0.81 g, 3.89 mmol), DMF (8 ml and 12 ml). The precipitate formed was filtered and re-crystallized from methanol to give 5-[3-(6-Chloro-7-hydroxy-4-oxo-4H-chromen-3-yl)-phenoxy]-pentanenitrile as a white solid (0.59 g, 59.1%); Rf 0.7 ethyl acetate/hexane (80/20)].

Workup

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

Sources & evidence

ORD record
ord-26b2800c7814468581fc9df09606dfd4
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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