Hydrochloric Acid → (4-Phenylbicyclo[2.2.2]oct-1-yl)acetic acid

HRID 908129Notes

Reaction equation

HRID 908129 reaction equation
[OH-:1].[K+].[C:3]1([C:9]23[CH2:16][CH2:15][C:12]([CH2:17][C:18]#N)([CH2:13][CH2:14]2)[CH2:11][CH2:10]3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[OH2:21]>C(O)CO>[C:3]1([C:9]23[CH2:16][CH2:15][C:12]([CH2:17][C:18]([OH:21])=[O:1])([CH2:13][CH2:14]2)[CH2:11][CH2:10]3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14797Potassium HydroxideHCID 67414049(4-Phenylbicyclo[2.2.2]oct-1-yl)acetonitrile

Product 1

HCID 21675351(4-Phenylbicyclo[2.2.2]oct-1-yl)acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
165 °C

Procedure

A solution of KOH (1.0 g, 17.52 mmol) in water (1.0 mL) was added to a suspension of (4-phenylbicyclo[2.2.2]oct-1-yl)acetonitrile (0.5 g) in ethylene glycol (10 mL) and the mixture stirred at 165° C. for 6 h, cooled, then poured in to water (100 mL). The mixture was acidified to pH 1 with conc. hydrochloric acid (˜0.5 mL) then extracted with ethyl acetate (100 mL then 30 mL). The combined extracts were washed with water (2×50 mL), dried (MgSO4) and concentrated down to give the title compound as a cream solid (0.5 g; 93%). 1H NMR (CDCl3) 1.57-1.69 (6H, m), 1.75-1.85 (6H, m), 2.12 (2H, s), 7.07-7.14 (1H, m), 7.19-7.28 (4H, m).

Workup

  1. temperaturecooled
  2. extractionthen extracted with ethyl acetate (100 mL
  3. washThe combined extracts were washed with water (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated down

Sources & evidence

ORD record
ord-f2fb3cb70e554f9faa4e47794ade8bd5
Source dataset
uspto-grants-2011_09
Patent number
US08017603B2

Reaction notes

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