Diethyl Ether → HCID 21904702, compound

HRID 1246615Notes

Reaction equation

HRID 1246615 reaction equation
[S-:1][C:2]#N.[NH4+].O.[CH3:6][C:7]1[CH:8]=[C:9]([OH:14])[CH:10]=[C:11]([CH:13]=1)[OH:12].C([O:17]CC)C>O.S([O-])([O-])(=O)=O.[Cu+2]>[OH:12][C:11]1[CH:13]=[C:7]([CH3:6])[C:8]2[S:1][C:2](=[O:17])[O:14][C:9]=2[CH:10]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 15666Ammonium thiocyanateHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 21904702HCID 21904702, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent

Procedure

Ammonium thiocyanate (10.71 g, 141 mmol) was added slowly to a solution of 5-methylresorcinol hydrate (5.0 g, 35 mmol) and copper(II) sulfate (17.56 g, 70 mmol) in water (100 mL), and the solution was stirred for 18 h. Diethyl ether (100 mL) was added and the mixture was filtered through Celite®, washing the cake with diethyl ether (100 mL). The diethyl ether layers were separated and the aqueous layer was re-extracted with diethyl ether (100 mL). The combined organic fractions were dried (MgSO4) and evaporated to a yellow-orange solid (5.30 g, 83%). 1H NMR showed the material to be 80–90% pure and this was taken on without further purification; δH (d6-DMSO, 400 MHz) 2.30 (3H, s), 6.57 (1H, s), 6.65 (1H, s), 9.90 (1H, brs).

Workup

  1. filtrationthe mixture was filtered through Celite®
  2. washwashing the cake with diethyl ether (100 mL)
  3. customThe diethyl ether layers were separated
  4. extractionthe aqueous layer was re-extracted with diethyl ether (100 mL)
  5. dry with materialThe combined organic fractions were dried (MgSO4)
  6. customevaporated to a yellow-orange solid (5.30 g, 83%)
  7. customthis was taken on without further purification

Sources & evidence

ORD record
ord-889345b2116b4f78ac4781a352024286
Source dataset
uspto-grants-2006_10
Patent number
US07129234B2

Reaction notes

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