Lithium Hydroxide → HCID 10709631, compound

HRID 1586215Notes

Reaction equation

HRID 1586215 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=2)[CH2:12][C:13]([O:15]C)=[O:14])=[CH:5][CH:4]=1)#[N:2].[Li+].[OH-]>CO.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=2)[CH2:12][C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10757911HCID 10757911, compound

Product 1

HCID 10709631HCID 10709631, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Part A. Methyl 4-(cyano)-beta-[3-(cyano)phenyl]benzene pentanoate (0.250 gm, 0.786 mmol) was dissolved in methanol and LiOH (0.056 gm, 2.3 mmol) in 1 mL of water was added. The solution was stirred at room temperature for 2 hrs. and extracted with ethyl acetate. The resultant aqueous layer was made acidic with 1 N HCl and extracted with ethyl acetate. The organic phase was dried over MgSO4 and concentrated to give 4-(cyano)-beta-[3-(cyano)phenyl]benzene pentanoic acid as an oil 0.138 gm (58%). 1H NMR (DMSO-d6): 1.95 (m, 2H), 2.3 (m, 3H), 2.70 (dd, 1H), 3.05 (m, 1H), 7.3 (d, 2H), 7.5 (t, 1H), 7.60 (d, 1H), 7.7 (m, 3H), 12.10 (s, 1H).

Workup

  1. extractionand extracted with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-708e11f64485472caa76e5c5974fedc4
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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