Sodium Chloride → 3-(3-Hydroxyprop-1-en-1-yl)benzonitrile

HRID 1709251Notes

Reaction equation

HRID 1709251 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[C:11](O)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(Cl)(=O)OCC.[Cl-].[Na+].[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C.O.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 133707983-Cyanocinnamic acid2×

Product 1

HCID 137333953-(3-Hydroxyprop-1-en-1-yl)benzonitrileYield 86.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

1.73 g of (E)-3-(3-cyanophenyl)acrylic acid was suspended in 8.7 ml of tetrahydrofuran. To the suspension was added 1.11 g of triethylamine. To the mixture was dropwise added a solution of 1.14 g of ethyl chlorocarbonate dissolved in 3.0 ml of tetrahydrofuran, at -20° to -10° C. The mixture was stirred for 30 minutes at 0° C. The reaction mixture was mixed with 2 ml of ethyl acetate and 20 ml of a saturated aqueous sodium chloride solution. The organic layer was separated and washed with a saturated aqueous sodium chloride solution to obtain a solution containing a mixed acid anhydride of (E)-3-(3-cyanophenyl)acrylic acid. To this solution was added 380 mg of sodium borohydride with ice-cooling. The mixture was stirred for 1 hour at the same temperature. To the reaction mixture was added 20 ml of water and 10 ml of ethyl acetate. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: n-hexane/acetone=5/1) to obtain 1.37 g of colorless oily (E)-3-(3-cyanophenyl)allyl alcohol.

Workup

  1. customThe organic layer was separated
  2. washwashed with a saturated aqueous sodium chloride solution
  3. customto obtain a solution
  4. temperaturecooling
  5. stirringThe mixture was stirred for 1 hour at the same temperature
  6. customThe organic layer was separated
  7. washwashed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe residue was purified by a column chromatography (eluant: n-hexane/acetone=5/1)

Sources & evidence

ORD record
ord-6645e65b2c85488cb142a503a3e92ed6
Source dataset
uspto-grants-1990_08
Patent number
US04948796

Reaction notes

Loading…