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Ethylene Glycol → alpha-Isopropyl-4-trifluoromethoxyphenylacetic acid

HRID 2050086
Notes
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Reaction equation

HRID 2050086 reaction equation
[CH:1]([CH:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1)[C:5]#N)([CH3:3])[CH3:2].[OH-:18].[K+].C(O)C[OH:22]>O>[CH:1]([CH:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1)[C:5]([OH:22])=[O:18])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 20343265HCID 20343265, compound

Product 1

HCID 20343284alpha-Isopropyl-4-trifluoromethoxyphenylacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
140 °C

Procedure

A mixture of α-isopropyl-4-trifluoromethoxyphenylacetonitrile (2.0 g), potassium hydroxide (3.0 g) in ethylene glycol (35 ml) and water (3 ml) is heated at 140° C. for 8 hours. The solution is poured into water and extracted with ether (2×10 ml). The aqueous layer is acidified with dilute hydrochloric acid and extracted with ether (3×10 ml), washed with water (1×25 ml), dried (Na2SO4) and evaporated to an oil (1.23 g); ir (neat) 1700 cm-1.

Workup

  1. extractionextracted with ether (2×10 ml)
  2. extractionextracted with ether (3×10 ml)
  3. washwashed with water (1×25 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated to an oil (1.23 g)

Sources & evidence

ORD record
ord-4398c650a46f43d98a0dc1be53200381
Source dataset
uspto-grants-1980_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04199595

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes