Hydrochloric Acid → HCID 135708803, compound

HRID 428333Notes

Reaction equation

HRID 428333 reaction equation
Cl.[NH2:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[N:17]([O-])=O.[Na+].[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=1[OH:29].[OH-].[Na+]>>[CH3:21][C:22]1[CH:27]=[C:26]([N:17]=[N:2][C:3]2[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=2[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:6])[CH:25]=[C:24]([CH3:28])[C:23]=1[OH:29]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 113352,6-DimethylphenolHCID 14798Sodium HydroxideHCID 760802-AminobenzophenoneHCID 23668193Sodium Nitrite

Product 1

HCID 135708803HCID 135708803, compound

Procedure

A slurry of ice (500 mL), hydrochloric acid (16.8 mL, 202 mmol, conc.), 2-aminobenzophenone (20.00 g, 101 mmol) and NaNO2 (9.0 g, 131 mmol) were added to a stirred solution of 2,6-dimethylphenol (18.40 g, 151 mmol) and sodium hydroxide (16.20 g, 404 mmol) in ice-cold water (100 mL). After 20 minutes the mixture was extracted with diethyl ether. The organic phase was washed with hydrochloric acid (6 M), NaHCO3(aq), dried (MgSO4) and the solvent evaporated. The crude residue was chromatographed on silica (toluene) and pure fractions were pooled and evaporated to give a red oil. The oil was crystallised in hexane/toluene to give 7.73 g (23%).

Workup

  1. extractionAfter 20 minutes the mixture was extracted with diethyl ether
  2. washThe organic phase was washed with hydrochloric acid (6 M), NaHCO3(aq)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated
  5. customThe crude residue was chromatographed on silica (toluene) and pure fractions
  6. customevaporated
  7. customto give a red oil
  8. customThe oil was crystallised in hexane/toluene
  9. customto give 7.73 g (23%)

Sources & evidence

ORD record
ord-63b893e365ca4df9b38a0aba349aeac6
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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