Sodium Hydroxide → HCID 21425148, compound

HRID 258985Notes

Reaction equation

HRID 258985 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 of ether
  4. washThe organic phases are washed until neutral,
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness in vacuo
  7. customRecrystallisation of the evaporation residue from ethanol

Sources & evidence

ORD record
ord-d2f52ca99bbe411baeed9938c5af84c8
Source dataset
uspto-grants-1977_07
Patent number
US04035413

Reaction notes

Loading…