Anisole → (1-Cyanocyclohexyl)acetic acid

HRID 1597682Notes

Reaction equation

HRID 1597682 reaction equation
C1(OC)C=CC=CC=1.[C:9]([C:11]1([CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)#[N:10]>FC(F)(F)C(O)=O>[C:9]([C:11]1([CH2:17][C:18]([OH:20])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)#[N:10]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 54503490HCID 54503490, compound

Product 1

HCID 11073797(1-Cyanocyclohexyl)acetic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2.4 mL (2.4 g, 22 mmol) of anisole in 50 mL of trifluoroacetic acid is added 5.00 g (22.4 mmol) of (1-cyanocyclohexyl)acetic acid, t-butyl ester. The reaction is monitored (TLC) for the loss of starting material and when the reaction is complete it is concentrated under reduced pressure. Water (˜10 mL) is added to the residue and the mixture is adjusted to pH=10-12 with base (NaOH). The basic aqueous layer is extracted with a suitable organic solvent (EtOAc) to remove impurities. The aqueous layer is acidified with acid (HCl) to pH=0-4 and extracted with a suitable solvent (EtOAc). The combined organic extracts of the acidified aqueous layer are dried and concentrated under reduced pressure to afford the product.

Workup

  1. concentrationis concentrated under reduced pressure
  2. additionWater (˜10 mL) is added to the residue
  3. extractionThe basic aqueous layer is extracted with a suitable organic solvent (EtOAc)
  4. customto remove impurities
  5. extractionextracted with a suitable solvent (EtOAc)
  6. customThe combined organic extracts of the acidified aqueous layer are dried
  7. concentrationconcentrated under reduced pressure
  8. customto afford the product

Sources & evidence

ORD record
ord-64689224114a48e9b3d36b97dc937d59
Source dataset
uspto-grants-2001_09
Patent number
US06294690B1

Reaction notes

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