Hydrochloric Acid → HCID 22904134, compound

HRID 1489214Notes

Reaction equation

HRID 1489214 reaction equation
S(OC)(O[CH3:5])(=O)=O.C[O:9][C:10](=[O:36])[CH2:11][O:12][C:13]1[C:18]([CH2:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][C:26]=3[Cl:30])[CH:21]=2)=[C:17]([OH:31])[C:16]([CH:32]=[O:33])=[C:15](C)[C:14]=1Cl.C(=O)([O-])[O-].[K+].[K+].Cl.[OH-].[K+]>CO.O.C1COCC1.CC(C)=O>[Cl:30][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:27]=1[CH:28]=[CH:29][C:20]([CH2:19][C:18]1[C:17]([O:31][CH3:5])=[C:16]([CH:32]=[O:33])[CH:15]=[CH:14][C:13]=1[O:12][CH2:11][C:10]([OH:9])=[O:36])=[CH:21]2

Participants

10

Reactant 5

HCID 313Hydrochloric Acid2×HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 54447199HCID 54447199, compound

Product 1

HCID 22904134HCID 22904134, compoundYield 43.1%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl sulfate (0.54 g, 4.3 mmol) was added dropwise into a mixture of [2-chloro-6-(5-chloro-naphthalen-2-ylmethyl)-4-formyl-5-hydroxy-3-methyl-phenoxy]-acetic acid methyl ester (0.76 g, 2.05 mmol), potassium carbonate (0.65 g, 4.8 mmol) and acetone (75 mL). The mixture was refluxed for 2 hours, poured into water, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation gave a yellow oil, which was dissolved in MeOH (15 mL), THF (15 mL) and treated with KOH (10%, 3.1 mL). After stirring for 4 hours the mixture was poured into water, acidified with HCl (2N), and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from hexane/EtOAc, gave an off-white solid (0.34 g, 43% yield, m.p. 191°-192° C.).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation
  5. customgave a yellow oil, which
  6. extractionextracted with EtOAc
  7. dry with materialThe organic extracts were dried over MgSO4
  8. customEvaporation and crystallization from hexane/EtOAc

Sources & evidence

ORD record
ord-645e7f37df954ca89fb671c571dbe3bc
Source dataset
uspto-grants-1997_10
Patent number
US05677342

Reaction notes

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