Acetic Acid → 2-Methoxy-4-(2-nitroethyl)phenol

HRID 2112297Notes

Reaction equation

HRID 2112297 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH:11]=[CH:12][N+:13]([O-:15])=[O:14])[CH:8]=[CH:7][C:6]=1[OH:16].C(O)(=O)C>O1CCOCC1.C(O)C.O>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH2:11][CH2:12][N+:13]([O-:15])=[O:14])[CH:8]=[CH:7][C:6]=1[OH:16]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 222082HCID 222082, compoundHCID 4311764Sodium borohydride

Product 1

HCID 230726552-Methoxy-4-(2-nitroethyl)phenol

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To sodium borohydride (4.3 g) suspended in a mixture of dioxane (85 ml) and ethanol (25 ml) at +10 to +15° C. is added 2-methoxy-4-(2-nitro-vinyl)-phenol in a mixture of dioxane (110 ml) and ethanol (50 ml). Thereafter the reaction mixture is stirred at room temperature for 2 hours. Acetic acid (4.5 ml) in water (130 ml) is then added carefully. The resulting mixture is evaporated to at about half of its volume. It is extracted with ethyl acetate (2×500 ml) washed with brine (2×100 ml) dried (MgSO4) and evaporated. 2-methoxy-4-(2-nitro-ethyl)-phenol is obtained as an oil which is purified by flash column chromatography on silica gel using ethyl acetate/hexane (1:1).

Workup

  1. customThe resulting mixture is evaporated to at about half of its volume
  2. extractionIt is extracted with ethyl acetate (2×500 ml)
  3. washwashed with brine (2×100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-e881fe07ae604e8eba7c32c8b3e2d423
Source dataset
uspto-grants-2009_04
Patent number
US07521579B2

Reaction notes

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