Hydrochloric Acid → HCID 13895882, compound

HRID 1106869Notes

Reaction equation

HRID 1106869 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[CH2:14][C:15](OC)=[O:16])([O-:3])=[O:2].[BH4-].[Na+].CO.Cl>O1CCCC1>[N+:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[CH2:14][CH2:15][OH:16])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312852methyl 2-(4,5-dimethoxy-2-nitrophenyl)acetateHCID 4311764Sodium borohydride

Product 1

HCID 13895882HCID 13895882, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A portion (3.4 g, 0.013 mol) of the methyl 2-nitro-4,5-dimethoxyphenylacetate produced in (2) above and sodium borohydride (2.52 g, 0.067 mol) were dissolved in tetrahydrofuran (100 ml), followed by heating at the reflux temperature for 30 min. Methanol (10 ml) was added dropwise to the reaction mixture over 30 min, followed by heating for 1 h. The mixture was cooled to room temperature and the residual reagents were decomposed with an aqueous solution of 1N HCl, followed by neutralization with an aqueous solution of sodium bicarbonate and three extractions with ethyl acetate. The organic extracts were dried with sodium sulfate and the solvent was evaporated, with the residue being purified by being subjected to column chromatography on silica gel using, as an eluent, ethyl acetate containing n-hexane (33%). The fractions containing the end product were collected and the solvent was evaporated to yield the end compound 2-nitro-4,5-dimethoxyphenethyl alcohol (3.0 g) as a pale yellow solid mass.

Workup

  1. temperatureby heating at the reflux temperature for 30 min
  2. temperatureby heating for 1 h
  3. extractionfollowed by neutralization with an aqueous solution of sodium bicarbonate and three extractions with ethyl acetate
  4. dry with materialThe organic extracts were dried with sodium sulfate
  5. customthe solvent was evaporated, with the residue
  6. custombeing purified
  7. additionethyl acetate containing n-hexane (33%)
  8. additionThe fractions containing the end product
  9. customwere collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-48b86efed460415b881cb529158829ae
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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