Hydrochloric Acid → HCID 13605833, compound

HRID 1589701Notes

Reaction equation

HRID 1589701 reaction equation
C([O:4][C:5]1[C:6]([CH3:34])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27]([Cl:33])[C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=1)([CH3:17])[CH2:9][CH2:8]2)(=O)C.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[Cl:33][CH:27]([CH2:26][C:23]1[CH:22]=[CH:21][C:20]([O:19][CH2:18][C:10]2([CH3:17])[CH2:9][CH2:8][C:7]3[C:12](=[C:13]([CH3:16])[C:14]([CH3:15])=[C:5]([OH:4])[C:6]=3[CH3:34])[O:11]2)=[CH:25][CH:24]=1)[C:28]([OH:30])=[O:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13605832HCID 13605832, compound

Product 1

HCID 13605833HCID 13605833, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

0.48 g of ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate was dissolved in a mixture of 5 ml of 99.5% ethanol and 2 ml of tetrahydrofuran. To this was added dropwise, under a nitrogen stream at 8°-10° C., a solution prepared by dissolving 133 mg of sodium hydroxide in 1 ml of 99.5% ethanol. When the whole of the solution had been added, the mixture was reacted for a further 18 hours at 0°-5° C., after which it was neutralized by adding to it dropwise a solution prepared by dissolving 0.37 g of concentrated hydrochloric acid in 1 ml of 99.5% ethanol. The solvent was then distilled off from the mixture under reduced pressure. The pale reddish oil thus separated was extracted with chloroform, and the chloroform extract was washed with water and then dried over anhydrous sodium sulfate. The crude product obtained by distilling the chloroform off under reduced pressure was subjected to silica gel column chromatography, and the desired 2-chloro-3-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]propionic acid was obtained from the fractions eluted with a 10:1 by volume mixture of benzene and ethyl acetate. Rf value on thin layer chromatography: 0.4 (tailing) [silica gel; developing solvent; benzene:99.5% ethanol=6:1 by volume]. Melting point 148°-149° C.

Workup

  1. additionTo this was added dropwise, under a nitrogen stream at 8°-10° C.
  2. customa solution prepared
  3. additionWhen the whole of the solution had been added
  4. customthe mixture was reacted for a further 18 hours at 0°-5° C.
  5. additionby adding to it dropwise a solution
  6. customprepared
  7. distillationThe solvent was then distilled off from the mixture under reduced pressure
  8. customThe pale reddish oil thus separated
  9. extractionwas extracted with chloroform
  10. extractionthe chloroform extract
  11. washwas washed with water
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe crude product obtained
  14. distillationby distilling the chloroform off under reduced pressure

Sources & evidence

ORD record
ord-508209f5c21a4990a0fb95037ddaa903
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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