Hydrochloric Acid → HCID 178525704, compound

HRID 528703Notes

Reaction equation

HRID 528703 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[O:13][N:12]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].Cl>O1CCOCC1>[O:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:11]([C@H:8]2[CH2:7][CH2:6][C@H:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)=[N:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178501069HCID 178501069, compound

Product 1

HCID 178525704HCID 178525704, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of trans-4-benzo[d]isoxazol-3-yl-cyclohexanecarboxylic acid methyl ester (6.77 g, 26.1 mmol) and aqueous 2 M sodium hydroxide solution (131 ml, 261 mmol) in 1,4-dioxane (261 ml) was stirred at room temperature for 20 h. The reaction mixture was cooled by addition of crushed ice (120 g) and acidified with concentrated hydrochloric acid (21.8 ml, 261 mmol). The reaction mixture was extracted with three 150-ml portions of ethyl acetate. The combined organic layers were washed with one 50-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude acid was crystallized from hot ethyl acetate to give the title compound (4.09 g, 64%) as white crystals. MS m/e: 246 ([M+14]+).

Workup

  1. extractionThe reaction mixture was extracted with three 150-ml portions of ethyl acetate
  2. washThe combined organic layers were washed with one 50-ml portion of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude acid was crystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-adc2af41c108464f8ae09de7e83784d3
Source dataset
uspto-grants-2016_05
Patent number
US09346824B2

Reaction notes

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