Hydrochloric Acid → 2-Cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid

HRID 502884Notes

Reaction equation

HRID 502884 reaction equation
C([O:3][C:4](=[O:29])[C:5]([C:27]#[N:28])([CH2:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][C:12]=1[N+:24]([O-:26])=[O:25])[CH2:6][CH2:7][CH:8]=[CH2:9])C.[Li+].[OH-].Cl>CO.O>[C:27]([C:5]([CH2:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][C:12]=1[N+:24]([O-:26])=[O:25])([CH2:6][CH2:7][CH:8]=[CH2:9])[C:4]([OH:29])=[O:3])#[N:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 574757172-Cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid ethyl ester2×

Product 1

HCID 574757182-Cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid ethyl ester (2.84 g, 7.20 mmol) was dissolved in methanol (42 mL). In a separate flask LiOH (1.5 g, 36.0 mmol) was dissolved in water (21 mL). The LiOH solution was added to the methanolic solution containing 2-cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid ethyl ester and the reaction was allowed to stir at room temperature for 2 hours. Next, 12N HCl (3 mL) was added to the reaction mixture followed by removal of the methanol under reduced pressure. The reaction mixture was poured into a separatory funnel, ethyl acetate was added and the organic layer washed 2 times with 1N HCl and one time with saturated brine solution. The organic layer was separated, dried with sodium sulfate, filtered and the solvent was removed to yield a residue.

Workup

  1. customfollowed by removal of the methanol under reduced pressure
  2. additionThe reaction mixture was poured into a separatory funnel
  3. additionethyl acetate was added
  4. washthe organic layer washed 2 times with 1N HCl and one time with saturated brine solution
  5. customThe organic layer was separated
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed
  9. customto yield a residue

Sources & evidence

ORD record
ord-1f4f3c287df741b2af5612b5da681308
Source dataset
uspto-grants-2010_08
Patent number
US07776882B2

Reaction notes

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