Sodium Hydroxide → 2-[p-(1-Cyclooctenyl)-phenoxy]-heptanoic acid

HRID 1764130

Reaction equation

HRID 1764130 reaction equation
C([O:3][C:4](=[O:26])[CH:5]([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)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])C.[OH-].[Na+]>C(O)C>[C:18]1([C:15]2[CH:14]=[CH:13][C:12]([O:11][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:4]([OH:26])=[O:3])=[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 54549182alpha-[p-(1-Cyclooctenyl)-phenoxy]-heptanoic acid ethyl ester

Product 1

HCID 542723602-[p-(1-Cyclooctenyl)-phenoxy]-heptanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 33 g of α-[p-(1-cyclooctenyl)-phenoxy]-heptanoic acid ethyl ester in 120 ml of ethanol are added 120 ml of 2N sodium hydroxide solutuion and the mixture is stirred for 11/2 hours at room temperature. The reaction mixture is then evaporated to dryness in vacuo and the residue partitioned between N hydrochloric acid and ether. The organic phase is washed until neutral, dried over sodium sulphate and evaporated to dryness in vacuo. The residue is crystallised from pentane to yield the 2-[p-(1-cyclooctenyl)-phenoxy]-heptanoic acid of the formula ##STR8## (m.p. 57°-60° C; b.p. 0.04 185°-188° C.

Workup

  1. customThe reaction mixture is then evaporated to dryness in vacuo
  2. customthe residue partitioned between N hydrochloric acid and ether
  3. washThe organic phase is washed until neutral,
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness in vacuo
  6. customThe residue is crystallised from pentane

Sources & evidence

ORD record
ord-59a83047f9844651896f37969df9d72b
Source dataset
uspto-grants-1978_09
Patent number
US04115416

Linked notes

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