Ammonium Chloride → HCID 68006201, compound

HRID 1026574Notes

Reaction equation

HRID 1026574 reaction equation
[C:1]([O:5][C:6](=[O:35])[C:7]([CH3:34])([CH3:33])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24]CC2C=CC=CC=2)=[O:23])=[C:18]([Cl:32])[CH:17]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].[Cl-].[NH4+]>ClCCl.O1CCCC1.O>[C:1]([O:5][C:6](=[O:35])[C:7]([CH3:34])([CH3:33])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[C:18]([Cl:32])[CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrate2×HCID 68006342HCID 68006342, compound

Product 1

HCID 68006201HCID 68006201, compoundYield 86.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a tetrahydrofuran (48 ml) and water (24 ml) mixed solvent suspension of benzyl 2′-(3-tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-chlorobiphenyl-4-carboxylate (2.40 g) was added lithium hydroxide monohydrate (224 mg). After the reaction solution was stirred at 60° C. for 17 hours, lithium hydroxide monohydrate (112 mg) was further added, and stirred at 60° C. for 6 hours. Tetrahydrofuran (40 ml) was further added, and stirred at 60° C. for 1 hour. After the reaction solution was brought back to room temperature, an aqueous ammonium chloride solution and dichloromethane were added, and the solution was separated. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Methanol was added to the resulting residue, and diluted with a large amount of water. The precipitated solid was collected by filtration and dried to afford 2′-(3-tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-chlorobiphenyl-4-carboxylic acid (1.69 g).

Workup

  1. stirringstirred at 60° C. for 6 hours
  2. stirringstirred at 60° C. for 1 hour
  3. customwas brought back to room temperature
  4. customthe solution was separated
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionMethanol was added to the resulting residue
  8. additiondiluted with a large amount of water
  9. filtrationThe precipitated solid was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-f11715dbcee144df86c6739f6f2fea4a
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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