Sodium Hydroxide → 5-[p-(1-Cyclooctenyl)-phenoxy]-pentanoic acid

HRID 597305

Reaction equation

HRID 597305 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:26])[CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=2)=[CH:14][CH:13]=1)C>C(O)C>[C:18]1([C:15]2[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:26])=[O:5])=[CH:17][CH:16]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 543745795-[p-(1-Cyclooctenyl)-phenoxy]-pentanoic acid ethyl ester

Product 1

HCID 545179805-[p-(1-Cyclooctenyl)-phenoxy]-pentanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 ml of 2 N sodium hydroxide solution are added to a solution of 15 g of 5-[p-(1-cyclooctenyl)-phenoxy]-pentanoic acid ethyl ester in 150 ml of ethanol and the mixture is left to stand at room temperature for 48 hours. It is then evaporated in vacuo to a volume of about 30 ml and the evaporation residue is distributed, at 5° C, between 100 ml of 2 N hydrochloric acid and twice 200 ml of ether. The organic phases are washed until neutral, dried over sodium sulphate and evaporated in vacuo. Crystallisation of the evaporation residue from ether-petroleum ether gives 5-[p-(1-cyclooctenyl)-phenoxy]-pentanoic acid of melting point 94- 96° C.

Workup

  1. waitthe mixture is left
  2. customIt is then evaporated in vacuo to a volume of about 30 ml
  3. customis distributed, at 5° C, between 100 ml of 2 N hydrochloric acid and twice 200 ml of ether
  4. washThe organic phases are washed until neutral,
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customCrystallisation of the evaporation residue from ether-petroleum ether

Sources & evidence

ORD record
ord-d7d3bf330b294cecb6711aba7ae304d3
Source dataset
uspto-grants-1977_03
Patent number
US04013708

Linked notes

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