Sodium Hydroxide → 4-Oxetan-3-yl-3-(2-m-tolyl-ethoxy)-benzoic Acid

HRID 1918333Notes

Reaction equation

HRID 1918333 reaction equation
C([O:4][C:5](=[O:26])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:15][O:14][CH2:13]2)=[C:8]([O:16][CH2:17][CH2:18][C:19]2[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=2)[CH:7]=1)(C)C.[OH-].[Na+]>CO>[O:14]1[CH2:15][CH:12]([C:9]2[CH:10]=[CH:11][C:6]([C:5]([OH:26])=[O:4])=[CH:7][C:8]=2[O:16][CH2:17][CH2:18][C:19]2[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 671701384-Oxetan-3-yl-3-(2-m-tolyl-ethoxy)-benzoic Acid Isopropyl Ester

Product 1

HCID 671687094-Oxetan-3-yl-3-(2-m-tolyl-ethoxy)-benzoic AcidYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

120 mg of 4-oxetan-3-yl-3-(2-m-tolyl-ethoxy)-benzoic acid isopropyl ester were dissolved in 3 ml of methanol and 0.2 ml of a 2 N aqueous solution of sodium hydroxide added. The mixture was left at room temperature for 6 days and then evaporated. The residue was dissolved in 10 ml of water, the pH adjusted to 2 with an aqueous sodium hydrogensulfate solution, and the mixture extracted three times using 20 ml each of DCM. The combined extracts were dried with magnesium sulfate and evaporated to yield 105 mg of the title compound.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in 10 ml of water
  3. extractionthe mixture extracted three times
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-c8d2e2a4461d48e29d093d79975bbc1f
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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