Hydrochloric Acid → 4-(1-Cyanocyclopropyl)benzoic acid

HRID 1971239Notes

Reaction equation

HRID 1971239 reaction equation
[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)#[N:2].Br[CH2:14][CH2:15]Br.Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+]>[C:1]([C:3]1([C:4]2[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=2)[CH2:15][CH2:14]1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 2708714-(Cyanomethyl)benzoic acid

Product 1

HCID 595567074-(1-Cyanocyclopropyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

To 2 g (12.4 mmol) of 4-(cyanomethyl)benzoic acid (Ubichem, Eastleigh, UK) and 10.9 ml (124 mmol) 1,2-dibromoethane (Fluka, Buchs, Switzerland) cooled at 0° C. with an ice-bath are added a solution of 14.4 g (62 mmol) benzyltriethylammonium chloride in 50 ml 8 M aqueous NaOH. The reaction mixture is stirred over night at rt and then is acidified at pH 1-2 with 6 M aqueous HCl and is extracted with EtOAc. The organic layer is washed with H2O (2×) and evaporated to dryness. The solid is triturated in MeOH to provide the crude title compound. ES-MS: 186 (M−H)−; analytical HPLC: tret=4.43 minutes (Grad 2).

Workup

  1. extractionis extracted with EtOAc
  2. washThe organic layer is washed with H2O (2×)
  3. customevaporated to dryness
  4. customThe solid is triturated in MeOH

Sources & evidence

ORD record
ord-4e3304f3832444b2b61eb9635277ce1a
Source dataset
uspto-grants-2013_04
Patent number
US08431592B2

Reaction notes

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