Resorcinol → Cladrin

HRID 1296874Notes

Reaction equation

HRID 1296874 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH2:19][C:20]([OH:22])=O)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:29]N(C=O)C>>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:19]2[C:20](=[O:22])[C:8]3[C:1](=[CH:3][C:4]([OH:5])=[CH:6][CH:7]=3)[O:2][CH:29]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

5

Reactant 4

HCID 5054ResorcinolHCID 6228DimethylformamideHCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 24819Phosphorus pentachloride

Product 1

HCID 5748605CladrinYield 80%

Procedure

This compounds was synthesised in the same manner as described above. Resorcinol (0.66 g, 6 mmol), 3,4-dimethoxy-phenylacetic acid (1.18 g, 6 mmol), BF3Et2O (4 ml), PCl5 (1.9 g, 9.1 mmol), DMF (5 ml and 10 ml). The precipitate formed was filtered and re-crystallized from methanol to give 3-(3,4-Dimethoxy-phenyl)-7-hydroxy-chromen-4-one as a pale orange solid (1.43 g, 80%); Rf 0.9 ethyl acetate/hexane (75/25).

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-c77a067264944db3951c4922a5c674b8
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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