Hydrochloric Acid → 4'-Cyano-6-methyl-biphenyl-3-carboxylic acid

HRID 1890248

Reaction equation

HRID 1890248 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)[C:8]([CH3:11])=[CH:9][CH:10]=1)=[O:4].[OH-].[Na+].Cl>O1CCOCC1.O>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:7]2[C:8]([CH3:11])=[CH:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)=[CH:13][CH:14]=1)#[N:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 594367074'-Cyano-6-methyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 594367094'-Cyano-6-methyl-biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 4′-cyano-6-methyl-biphenyl-3-carboxylic acid methyl ester 2 (2.56 g, 10.3 mmol) in 1,4-dioxane-H2O (1:1 mixture, 20 ml) is added NaOH (1.22 g, 30.2 mmol)). The reaction is stirred at ambient temperature for 24 hours. To this mixture is added aqueous HCl (1 N, 36 ml) and it is then extracted with ethyl acetate (40 ml×3). The organic layers are combined, dried over anhydrous Na2SO4. The solver is removed. The solid obtained is washed with small amount of acetonitrile and air dried to give 4′-cyano-6-methyl-biphenyl-3-carboxylic acid 3: 1H NMR (DMSO-d6) δ 7.94 (d, 2H, J=8.0 Hz), 7.84 (dd, 1H, J1=8.4 Hz, J2=1.2 Hz), 7.75 (d, 1H, J=1.2 Hz), 7.61 (d, 2H, J=8.0 Hz), 7.48 (d, 1H, J=8.4 Hz), 2.29 (s, 3H); LC-MS m/z 238.1 (M+1).

Workup

  1. extractionis then extracted with ethyl acetate (40 ml×3)
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solver is removed
  4. customThe solid obtained
  5. washis washed with small amount of acetonitrile and air
  6. customdried

Sources & evidence

ORD record
ord-3f7ac7a1fa5b40d4be69ebd05a309c5d
Source dataset
uspto-grants-2013_08
Patent number
US08507471B2

Linked notes

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