Hydrochloric Acid → HCID 22506856, compound

HRID 985583Notes

Reaction equation

HRID 985583 reaction equation
[C:1]([C:5]1[C:6]([OH:19])=[C:7]([CH2:15][C:16]([CH3:18])=[CH2:17])[C:8]([CH3:14])=[C:9]([NH:11]C=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[OH-].[Na+]>CO>[NH2:11][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]2[O:19][C:16]([CH3:18])([CH3:17])[CH2:15][C:7]=2[C:8]=1[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22506853HCID 22506853, compound

Product 1

HCID 22506856HCID 22506856, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-[5-(tert-butyl)4-hydroxy-2-methyl-3-(2-methyl-2-propenyl)phenyl]formamide (10.45 g, 40 mmol) in methanol (100 ml) was added concentrated hydrochloric acid (40 ml) and the mixture was heated under reflux for 3 hours under argon atmosphere. After cooling to 0° C., the mixture was made weakly basic using 12N sodium hydroxide, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate, and then the solvent was removed under reduced pressure. The residue was purified by a column chromatography on a silica gel (hexane:ethyl acetate=1:1) and crystallized from hexane to obtain 6.28 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours under argon atmosphere
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by a column chromatography on a silica gel (hexane:ethyl acetate=1:1)
  8. customcrystallized from hexane

Sources & evidence

ORD record
ord-30dfe4355837473eb510b29b1e2b3126
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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