Ethyl 5-bromovalerate → 5-[p-(1-Cyclooctenyl)-phenoxy]-pentanoic acid ethyl ester

HRID 597304

Reaction equation

HRID 597304 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[Na].[CH2:17]([O:19][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24]Br)[CH3:18]>C(O)C>[CH2:17]([O:19][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][O:15][C:12]1[CH:11]=[CH:10][C:9]([C:1]2[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2)=[CH:14][CH:13]=1)[CH3:18]

Participants

5

Reactant 3

HCID 84580Ethyl 5-bromovalerateHCID 5360545SodiumHCID 53964233p-(1-Cyclooctenyl)-phenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12 g of p-(1-cyclooctenyl)-phenol are first added to a solution of 1.7 g of sodium in 60 ml of absolute ethanol whilst stirring in an anhydrous atmosphere, and after 30 minutes 18.8 g of 5-bromopentanoic acid ethyl ester are added dropwise. After completion of the addition, the mixture is stirred for 15 hours at 70° C and is evaporated to dryness in vacuo. The evaporation residue is distributed between 3 times 150 ml of ether and twice 100 ml of water. The organic phases are combined, dried over sodium sulphate and evaporated in vacuo. Chromatography of the evaporation residue on silica gel with chloroform as the eluant gives 5-[p-(1-cyclooctenyl)-phenoxy]-pentanoic acid ethyl ester of boiling point 165° -170° C at 0.03 mm Hg.

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture is stirred for 15 hours at 70° C
  3. customis evaporated to dryness in vacuo
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a3789e0bc05e4e07864f7cb6f1be5937
Source dataset
uspto-grants-1977_03
Patent number
US04013708

Linked notes

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