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

HRID 2112298Notes

Reaction equation

HRID 2112298 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>C(O)C.O1CCCC1.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)phenolYield 95.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To sodium borohydride (1.93 g, 51.2 mmol) suspended in ethanol (15 ml) at +10 to +15° C. is added a solution of 2-methoxy-4-(2-nitro-vinyl)-phenol (10.0 g, 51.2 mmol) in tetrahydrofuran (100 ml) over 1 h. Thereafter the reaction mixture is stirred at room temperature for 30 minutes. Acetic acid (4 ml) in water (100 ml) is then added carefully. The resulting mixture is evaporated to at about a quarter of its volume. It is extracted with ethyl acetate (1×100 ml, 1×50 ml) washed with brine (2×50 ml) dried (Na2SO4) and evaporated. 2-methoxy-4-(2-nitro-ethyl)-phenol (9.64 g) is obtained as an oil, which is purified by kugelrohr distillation (+150° C., 0.02 torr) yielding 7.3 g (72%) of purified material.

Workup

  1. customThe resulting mixture is evaporated to at about a quarter of its volume
  2. extractionIt is extracted with ethyl acetate (1×100 ml, 1×50 ml)
  3. washwashed with brine (2×50 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-45a79b03fbb14fbeaf9a1248cd6783c3
Source dataset
uspto-grants-2009_04
Patent number
US07521579B2

Reaction notes

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