HCID 53883975, compound → HCID 21425160, compound

HRID 1974201Notes

Reaction equation

HRID 1974201 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[C:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2)C>C(O)C.[OH-].[Na+]>[C:16]12([C:10]3[CH:11]=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=3[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:26])=[O:3])[CH2:23][CH:22]3[CH2:24][CH:18]([CH2:19][CH:20]([CH2:21]3)[CH2:25]1)[CH2:17]2

Participants

4

Reactant 1

HCID 53883975HCID 53883975, compound

Product 1

HCID 21425160HCID 21425160, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 7.9 g of 4-[2-(1-adamantyl)-5-methylphenoxy]-butyric acid ethyl ester in 80 ml of ethanol and 80 ml of 1 N sodium hydroxide solution is left to stand for 60 hours at about 25° C. It is then evaporated to dryness in vacuo and the evaporation residue is partitioned between 100 ml of 2 N hydrochloric acid and twice 200 ml of ether. The organic phases are washed until neutral, treated with active charcoal, dried over sodium sulphate and evaporated in vacuo. Crystallising the evaporation residue twice from ether-petroleum ether gives 4-[2-(1-adamantyl)-5-methylphenoxy]-butyric acid of melting point 147°-150° C.

Workup

  1. customIt is then evaporated to dryness in vacuo
  2. customthe evaporation residue is partitioned between 100 ml of 2 N hydrochloric acid and twice 200 ml of ether
  3. washThe organic phases are washed until neutral,
  4. additiontreated with active charcoal
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customCrystallising the evaporation residue twice from ether-petroleum ether

Sources & evidence

ORD record
ord-92f087e0c3cc45d6bb4bb9e0198af484
Source dataset
uspto-grants-1976_12
Patent number
US04000144

Reaction notes

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