Acetic Acid → 1-Benzyloxy-4-(2-nitro-ethyl)-benzene

HRID 1694233Notes

Reaction equation

HRID 1694233 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.CS(C)=O.[B-].[Na+]>O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 5702926(E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzeneHCID 22959485Vertellus

Product 1

HCID 247210371-Benzyloxy-4-(2-nitro-ethyl)-benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

While cooling using a water bath, to a mixture of 1-benzyloxy-4-((E)-2-nitro-vinyl)-benzene described in Manufacturing Example 229-1-1 (60 g, 0.23 mol), acetic acid (27 mL) and dimethyl sulfoxide (400 mL) was added sodium borohydrate (8.9 g, 0.23 mol), which was stirred for 20 minutes at room temperature. Water (2.5 L) was added dropwise to the reaction mixture, and the deposited solids were filtered. Diethyl ether (300 mL) was added to the obtained solids to dissolve the title compound, and separation into filtrate and solids was carried out by filtration. The filtrate was concentrated under a reduced pressure to obtain the title compound (39 g). On the other hand, diethyl ether (300 mL) was added to the previously separated solid to dissolve the title compound, and separation into filtrate and solids was carried out by filtration. The filtrate was concentrated under a reduced pressure to obtain the title compound (12 g). This was combined with the previously obtained solids to obtain the title compound (51 g) as a crude product.

Workup

  1. temperatureWhile cooling
  2. filtrationthe deposited solids were filtered
  3. additionDiethyl ether (300 mL) was added to the obtained solids
  4. dissolutionto dissolve
  5. customthe title compound, and separation into filtrate and solids
  6. filtrationwas carried out by filtration
  7. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-cb917808b608462a9245b8af6fa218d1
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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