Hydrochloric Acid → HCID 18368290, compound

HRID 417359Notes

Reaction equation

HRID 417359 reaction equation
C([Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[O:21][CH3:22])(C)C)(C)(C)C.Cl>C1COCC1>[CH3:22][O:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[O:11][CH2:10][CH2:9][OH:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66625360HCID 66625360, compound

Product 1

HCID 18368290HCID 18368290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl-[2-(2-methoxy-4-nitro-phenoxy)-ethoxy]-dimethyl-silane (9 g, 27.5 mmol) in THF (10 mL) was added an aqueous HCl solution (2 N, 10 mL, 20 mmol). The reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated. The residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 solution. The organic layer was separated, and aqueous layer was extracted with ethyl acetate. The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated to give 2-(2-methoxy-4-nitrophenoxy)ethanol as a off white solid (5.5 g, 94%).

Workup

  1. concentrationThe mixture was concentrated
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 solution
  3. customThe organic layer was separated
  4. extractionaqueous layer was extracted with ethyl acetate
  5. extractionThe combined organic extract
  6. washwas washed with water, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0ad7bc59f9914d1ca4082b4898f0c90c
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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