Hydrochloric Acid → HCID 4186956, compound

HRID 2061431Notes

Reaction equation

HRID 2061431 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](Cl)(=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11].Cl>[OH-].[Na+].C1(C)C=CC=CC=1>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 115683-AminophenolHCID 62493Pivaloyl chloride

Product 1

HCID 4186956HCID 4186956, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-amino-phenol (60 g, 6.55 mol) in 2 N NaOH (1 l), cooled to 10° C., pivaloyl chloride (68 ml, 0.55 mol) in toluene (200 ml) is added within 1 h. After stirring for 15 h at 25° C., the mixture is cooled to 0° C. and acidified to pH 1 with conc. HCl. Extraction with EtOAc washing with water, 10% NaHCO3, water, and brine, followed by drying (Na2SO4), evaporation of volatiles, and crystallization (EtOAc/hexanes) gives N-(3-hydroxy-phenyl)-2,2-dimethyl-propionamide. N-(3-Hydroxy-phenyl)-2,2-dimethyl-propionamide (49 g, 0.254 mol) in dichloromethane (1 l) is treated with dihydropyrane (66 ml, 0.762 mol) and pyridinium p-toluenesulfonate (957 mg, 3.8 mmol). After stirring for 6 days at 25° C., the solvent is removed and the residue crystallized from EtOAc/hexanes to give 2,2-dimethyl-N-[3-(tetrahydro-pyran-2-yloxy)-phenyl]-propionamide.

Workup

  1. temperaturethe mixture is cooled to 0° C.
  2. extractionExtraction with EtOAc washing with water, 10% NaHCO3, water, and brine
  3. customby drying
  4. custom(Na2SO4), evaporation of volatiles, and crystallization (EtOAc/hexanes)

Sources & evidence

ORD record
ord-1386570c9c1a4144802a120abba4f35a
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

Loading…