Hydrochloric Acid → 1-[3-Tert-butyl-5-(2-methoxyethoxy)phenyl]ethanone

HRID 532380Notes

Reaction equation

HRID 532380 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([O:17][CH2:18][CH2:19][O:20][CH3:21])[CH:16]=1)[C:8](N(OC)C)=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH3:22][Mg]Br.Cl>C1COCC1.O>[C:1]([C:5]1[CH:6]=[C:7]([C:8](=[O:9])[CH3:22])[CH:14]=[C:15]([O:17][CH2:18][CH2:19][O:20][CH3:21])[CH:16]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 581368013-tert-butyl-N-methoxy-5-(2-methoxyethoxy)-N-methylbenzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 581368081-[3-Tert-butyl-5-(2-methoxyethoxy)phenyl]ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-tert-Butyl-N-methoxy-5-(2-methoxyethoxy)-N-methylbenzamide (O3.043; 1.35 g) was dissolved in THF (40 ml), methylmagnesium bromide (3.05 ml, 3 M in ether) was added dropwise at 0° C. and then the mixture was stirred at RT for 2 h. Then the mixture was admixed with 1 N hydrochloric acid (50 ml), diluted with water and extracted by shaking three times with EA. Then the combined EA phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (40 g cartridge, n-heptane/EA gradient of 0-30% in 30 min). 1.0 g of the title compound were obtained.

Workup

  1. extractionextracted
  2. stirringby shaking three times with EA
  3. dry with materialThen the combined EA phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customsilica gel (40 g cartridge, n-heptane/EA gradient of 0-30% in 30 min)

Sources & evidence

ORD record
ord-51cdb4316a464836ac5a55e7e965462a
Source dataset
uspto-grants-2014_10
Patent number
US08853206B2

Reaction notes

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