Ethanol → HCID 23035272, compound

HRID 1709993Notes

Reaction equation

HRID 1709993 reaction equation
[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[C:12]([CH:18]=1)[C:13]([O:15]CC)=[O:14])[CH2:4][CH2:5][CH3:6].C(O)C>O>[CH2:3]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:19][CH2:20][C:21]([F:22])([F:23])[F:24])=[C:12]([CH:18]=1)[C:13]([OH:15])=[O:14])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 23035338HCID 23035338, compound

Product 1

HCID 23035272HCID 23035272, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.5 g (0.062 mole) of sodium hydroxide in 60 ml of water was combined with 9.9 g (0.031 mole) of ethyl 5-butoxy-2-(2,2,2-trifluoroethoxy)benzoate and 50 ml of ethanol. The reaction mixture was heated at reflux for about sixteen hours then concentrated to remove most of the ethanol, diluted with water and acidified with 10% hydrochloric acid. The resulting solid was collected then recrystallized from a mixture of ethanol and water to provide 7.0 g of white crystalline 5-butoxy-2-(2,2,2-trifluoroethoxy)benzoic acid, m.p. 88.5°-90° C. Analysis: Calculated for C13H15F3O4 : %C, 53.4; %H. 5.2; Found: %C, 53.3; %H, 5.0.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for about sixteen hours
  3. concentrationthen concentrated
  4. customto remove most of the ethanol
  5. additiondiluted with water
  6. customThe resulting solid was collected
  7. customthen recrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-af9c09de84f949229d0d2f9d97c7bcf0
Source dataset
uspto-grants-1990_08
Patent number
US04952574

Reaction notes

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