Sodium Hydroxide → HCID 53703180, compound

HRID 597302Notes

Reaction equation

HRID 597302 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:25])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=2)=[CH:13][CH:12]=1)C>C(O)C>[C:17]1([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][C:6]([OH:25])=[O:5])=[CH:16][CH:15]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54471875HCID 54471875, compound

Product 1

HCID 53703180HCID 53703180, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50 ml of 2 N sodium hydroxide solution are added to a solution of 21 g of crude 4-[p-(1-cyclooctenyl)-phenoxy]-butyric acid ethyl ester in 300 ml of ethanol, whilst stirring, and the mixture is stirred for 48 hours and evaporated to dryness under reduced pressure. The evaporation residue is distributed 3 times between 200 ml of ether and 200 ml of water in each case and the water phases are acidified to pH = 2 with concentrated hydrochloric acid and extracted with 3 times 200 ml of ether. The resulting organic phases are combined, washed until neutral, dried over sodium sulphate and evaporated under reduced pressure. The evaporation residue, after treatment with active charcoal and crystallisation from ether-petroleum ether, gives 4-[p-(1-cyclooctenyl)-phenoxy]-butyric acid in the form of white needles of melting point 110° -111° C.

Workup

  1. stirringthe mixture is stirred for 48 hours
  2. customevaporated to dryness under reduced pressure
  3. extractionextracted with 3 times 200 ml of ether
  4. washwashed until neutral,
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customThe evaporation residue, after treatment with active charcoal and crystallisation from ether-petroleum ether

Sources & evidence

ORD record
ord-c698d9315d304925b445a1e1e7a9332a
Source dataset
uspto-grants-1977_03
Patent number
US04013708

Reaction notes

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