Sodium Hydroxide → HCID 13037787, compound

HRID 1156636Notes

Reaction equation

HRID 1156636 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:26])[CH2:19][C:20](=[O:25])[C:21]([O:23]C)=[O:22])=[CH:14][CH:13]=2)[CH:7]=[CH:8][C:9]=1[Cl:10]>O1CCCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18](=[O:26])[CH2:19][C:20](=[O:25])[C:21]([OH:23])=[O:22])=[CH:16][CH:17]=2)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13037783HCID 13037783, compound

Product 1

HCID 13037787HCID 13037787, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

There was dissolved in 15 ml of tetrahydrofuran and 3.75 ml of 2 N sodium hydroxide 1.09 g (3 mMol) of the ester product prepared in Step B above; and the reaction mixture was stirred overnight at room temperature, whereupon a solid precipitated. Then, 4 ml of 2 N hydrochloric acid was added, and the mixture was stirred well. The tetrahydrofuran layer was then separated, and the aqueous layer was extracted twice with 20 ml of diethyl ether. The combined organic layers were dried and evaporated. The oily residue solidified on standing. The material was crystallized from carbon tetrachloride, whereupon a yellow solid was obtained (370 mg), m.p. 133°-140° C. The material was crystallized again from carbon tetrachloride, m.p. 142°-144° C. Analysis:

Workup

  1. customprecipitated
  2. additionThen, 4 ml of 2 N hydrochloric acid was added
  3. stirringthe mixture was stirred well
  4. customThe tetrahydrofuran layer was then separated
  5. extractionthe aqueous layer was extracted twice with 20 ml of diethyl ether
  6. customThe combined organic layers were dried
  7. customevaporated
  8. customThe material was crystallized from carbon tetrachloride, whereupon a yellow solid
  9. customwas obtained (370 mg), m.p. 133°-140° C
  10. customThe material was crystallized again from carbon tetrachloride, m.p. 142°-144° C

Sources & evidence

ORD record
ord-b77844c705794b5099fc69c90a0965cc
Source dataset
uspto-grants-1982_06
Patent number
US04336397

Reaction notes

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