Ethanol → HCID 18451535, compound

HRID 1270796Notes

Reaction equation

HRID 1270796 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([I:12])=[C:7](CC#N)[CH:8]=1.[OH-:15].[Na+].[CH2:17]([OH:19])[CH3:18]>O>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([I:12])=[C:7]([CH2:18][C:17]([OH:15])=[O:19])[CH:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 18451536HCID 18451536, compound

Product 1

HCID 18451535HCID 18451535, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-trifluoromethyl-2-iodophenylacetonitrile (30 g, 96 mmol) in ethanol (100 mL) is stirred at room temperature. Sodium hydroxide (7.7 g, 192 mmol) dissolved in water (60 mL) is added. The mixture is heated to reflux temperature for 12 hours and then cooled to room temperature. Most of the ethanol is removed using a rotary evaporator and the residual aqueous solution adjusted to pH 4 with 3 N HCl. The solid which forms is isolated by filtration and washed with water (250 mL) and then hexanes (500 mL). Air drying gives 5-trifluoromethyl-2-iodophenylacetic acid.

Workup

  1. additionis added
  2. temperatureThe mixture is heated
  3. temperatureto reflux temperature for 12 hours
  4. customMost of the ethanol is removed
  5. customa rotary evaporator
  6. customThe solid which forms is isolated by filtration
  7. washwashed with water (250 mL)
  8. customAir drying

Sources & evidence

ORD record
ord-3b87cc01fe4a4345bab7b1e20a9ac259
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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