Sodium Hydroxide → HCID 68453271, compound

HRID 658100Notes

Reaction equation

HRID 658100 reaction equation
[CH3:1][C:2]1([CH3:19])[O:6][CH:5]([C:7]2[C:8]([F:18])=[C:9]([CH:15]=[CH:16][CH:17]=2)[C:10]([O:12]CC)=[O:11])[CH2:4][O:3]1.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:19])[O:6][CH:5]([C:7]2[C:8]([F:18])=[C:9]([CH:15]=[CH:16][CH:17]=2)[C:10]([OH:12])=[O:11])[CH2:4][O:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68452985HCID 68452985, compound

Product 1

HCID 68453271HCID 68453271, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 5.46 g portion of ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluorobenzoate was dissolved in 100 ml of THF and cooled to 0° C., and then 40.8 ml of 1 N sodium hydroxide aqueous solution was slowly added thereto. This was risen to room temperature and further stirred for 17 hours. After evaporation of THF, the residue was cooled to 0° C. and acetic acid was slowly added thereto until the pH value became 3 to 4. This was extracted with diethyl ether, dried with sodium sulfate and concentrated, and then subjected to azeotropic treatment three times with Tol, thereby obtaining 4.66 g (95%) of 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluorobenzoic acid (Reference Example 11-1). FN: 239

Workup

  1. customThis was risen to room temperature
  2. customAfter evaporation of THF
  3. temperaturethe residue was cooled to 0° C.
  4. additionacetic acid was slowly added
  5. extractionThis was extracted with diethyl ether
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b2c7852ba8674ca7a75302bee2bd1fe2
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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