Sodium Hydroxide → HCID 21425148, compound

HRID 1974209Notes

Reaction equation

HRID 1974209 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH:22]3[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:24][CH:16]2[CH2:17]4)[CH2:21]3)=[CH:11][CH:10]=1)C.[OH-].[Na+]>C(O)C>[CH:22]12[CH2:21][CH:20]3[CH2:19][CH:18]([CH2:17][CH:16]([CH2:24]3)[CH:15]1[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:25])=[O:3])=[CH:14][CH:13]=1)[CH2:23]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54249896HCID 54249896, compound

Product 1

HCID 21425148HCID 21425148, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7.2 g of 4-[4-(2-adamantyl)-phenoxy]-butyric acid ethyl ester in 150 ml of ethanol is mixed with 150 ml of sodium hydroxide solution and the mixture is left to stand for 24 hours at 30° C. The reaction solution is then evaporated to dryness in vacuo and the evaporation residue is partitioned between 100 ml of 2 N hydrochloric acid and twice 100 ml. of ether. The organic phases are washed until neutral, dried over sodium sulphate and evaporated to dryness in vacuo. - Recrystallisation of the evaporation residue from ethanol gives 4-[4-(2-adamantyl)-phenoxy]-butyric acid of melting point 163°-165° C.

Workup

  1. waitthe mixture is left
  2. customThe reaction solution is then evaporated to dryness in vacuo
  3. customthe evaporation residue is partitioned between 100 ml of 2 N hydrochloric acid and twice 100 ml
  4. washThe organic phases are washed until neutral,
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness in vacuo
  7. custom- Recrystallisation of the evaporation residue from ethanol

Sources & evidence

ORD record
ord-99e1d6c5e8704c229ac584ed79f87eb4
Source dataset
uspto-grants-1976_12
Patent number
US04000144

Reaction notes

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