Ethanol → 3-Trifluoromethyl-4-(2-(S)-butoxy)benzoic acid

HRID 1268926Notes

Reaction equation

HRID 1268926 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=C([CH:8]=[CH:9][C:10]=1[O:11][C@H:12]([CH2:14][CH3:15])[CH3:13])C#N.[OH-:18].[Na+].[CH3:20][CH2:21][OH:22]>>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:20]([CH:8]=[CH:9][C:10]=1[O:11][C@H:12]([CH2:14][CH3:15])[CH3:13])[C:21]([OH:18])=[O:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 184469513-Trifluoromethyl-4-(2-(S)-butoxy)benzonitrile

Product 1

HCID 184469503-Trifluoromethyl-4-(2-(S)-butoxy)benzoic acid

Conditions

Temperature
80 °C

Procedure

A solution of 550 mg (2.2 mmol) of 3-trifluoromethyl-4-(2-(S)-methylpropyloxy)benzonitrile (from Step A) in 5 mL of EtOH was treated with 1.5 mL of 5.0 N NaOH and was heated to 80° C. for 3 h. The reaction was then concentrated, treated with 2 N HCl, extracted with 30 mL of EtOAc, dried over MgSO4 and concentrated which afforded 600 mg of the title compound: 1H NMR (500 Mhz) δ 0.99 (t, J=7.3, 3H), 1.43 (d, J=5.9, 3H), 1.73–1.83 (m, 2H), 4.54 (septet, 1H), 7.02 (d, J=8.9, 1H), 8.21 (d, J=8.9, 1H), 8.32 (s, 1H).

Workup

  1. concentrationThe reaction was then concentrated
  2. additiontreated with 2 N HCl
  3. extractionextracted with 30 mL of EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated which

Sources & evidence

ORD record
ord-9606960b1e0146e4b90a95282714092c
Source dataset
uspto-grants-2007_04
Patent number
US07199142B2

Reaction notes

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