Anisole → (1-Cyanocyclohexyl)acetic acid

HRID 1862584Notes

Reaction equation

HRID 1862584 reaction equation
C1(OC)C=CC=CC=1.[C:9]([C:11]1([CH2:17][C:18]([O:20]CCCC)=[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 57003026HCID 57003026, 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, 1-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-b3bcf251663e421ab61df04e79981a4c
Source dataset
uspto-grants-2003_03
Patent number
US06538148B2

Reaction notes

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