Hydrochloric Acid → HCID 67080204, compound

HRID 1021565Notes

Reaction equation

HRID 1021565 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:33])[NH:20][CH2:21][CH2:22][C:23]3[C:28]([O:29][CH3:30])=[CH:27][C:26]([Cl:31])=[CH:25][C:24]=3[Cl:32])=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:34]([O-:36])=[O:35].[OH-].[Na+].Cl.[Na].C[O-].[Na+]>O1CCCC1.C(O)C.CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:33])[NH:20][CH2:21][CH2:22][C:23]3[C:28]([O:29][CH3:30])=[CH:27][C:26]([Cl:31])=[CH:25][C:24]=3[Cl:32])=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:34]([OH:36])=[O:35]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 86653239HCID 86653239, compound

Product 1

HCID 67080204HCID 67080204, compoundYield 101.1%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 6-chloro-7-(4-(2,4-dichloro-6-methoxyphenethylcarbamoyl)phenoxy)chroman-4-carboxylate (0.56 g; 0.97 mmol) in a mixture of 10 mL tetrahydrofuran and 5 mL ethanol at ambient temperature was added 3.9 mL of 1M aqueous sodium hydroxide. The resulting slightly cloudy mixture was vigorously stirred at ambient temperature the reaction mixture was poured into a separatory funnel containing 100 mL ethyl acetate and 50 mL 1M aqueous hydrochloric acid. After shaking, the organic layer was washed with 20 mL brine, then dried over sodium sulfate and evaporated to give 0.60 of light yellow oil. To convert to the sodium salt, the material was dissolved in 10 mL methanol, and 0.22 mL of 25% sodium methoxide in methanol was added. The solvent was evaporated, and the residue evaporated from ether to give 0.54 g of 6-chloro-7-(4-(2,4-dichloro-6-methoxyphenethylcarbamoyl) phenoxy)chroman-4-carboxylic acid as an off-white glass. MS (apci, pos) m/z=550. MS (apci, neg) m/z=548.

Workup

  1. additionwas poured into a separatory funnel
  2. stirringAfter shaking
  3. washthe organic layer was washed with 20 mL brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give 0.60 of light yellow oil
  7. customThe solvent was evaporated
  8. customthe residue evaporated from ether

Sources & evidence

ORD record
ord-88aeb623270e45a18bf3f46d2695de0a
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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