Acetic Acid → HCID 13988397, compound

HRID 1030639Notes

Reaction equation

HRID 1030639 reaction equation
[BH4-].[Na+].[N+:3]([CH:6]=[CH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)([O-:5])=[O:4].C(O)(=O)C>O1CCOCC1.C(O)C>[N+:3]([CH2:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)([O-:5])=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 269865HCID 269865, compoundHCID 4311764Sodium borohydride

Product 1

HCID 13988397HCID 13988397, compoundYield 6.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of sodium borohydride (4 g) in a mixture of dioxane (85 ml) and ethanol (30 ml) was added dropwise a solution of 2-(2-nitroethenyl)naphthalene (100 g) in dioxane (90 ml) over 30 minutes. The flask was cooled with a cold water bath during addition. Stirring was maintained for an additional 11/2 hours. Ice (100 ml) and 50% aqueous acetic acid (12 ml) were added and the mixture was stirred for 2 hours at room temperature, concentrated in vacuo and extracted with methylene chloride. The organic layer was washed with water, saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was evaporated in vacuo to yield an oil which was crystallized from acetic acid to give the title compound (6.79 g) as a yellow solid, m.p. 59-60° C.

Workup

  1. temperatureThe flask was cooled with a cold water bath during addition
  2. temperaturewas maintained for an additional 11/2 hours
  3. stirringthe mixture was stirred for 2 hours at room temperature
  4. concentrationconcentrated in vacuo
  5. extractionextracted with methylene chloride
  6. washThe organic layer was washed with water, saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated in vacuo
  9. customto yield an oil which
  10. customwas crystallized from acetic acid

Sources & evidence

ORD record
ord-4308ffed0bb14b7288f29d62eb9f1f99
Source dataset
uspto-grants-1992_04
Patent number
US05106861

Reaction notes

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