Sodium Hydroxide → HCID 54496197, compound

HRID 1764132Notes

Reaction equation

HRID 1764132 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])C.[OH-].[Na+]>C(O)C>[C:19]1([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:4]([OH:27])=[O:3])=[CH:18][CH:17]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54097726HCID 54097726, compound

Product 1

HCID 54496197HCID 54496197, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 34 g of α-[p-(1-cyclooctenyl)-phenoxy]-octanoic acid ethyl ester in 120 ml of ethanol are added 120 ml of 2N sodium hydroxide solution and the mixture is stirred for 11/2hours 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 distilled at 0.07 mm/205°-210° C. The distillate is crystallised from pentane at 0° C to yield the α-[p-(1-cyclooctenyl)-phenoxy]-octanoic acid of the formula ##STR10## which melts at 55°-57° 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. distillationThe residue is distilled at 0.07 mm/205°-210° C
  7. customThe distillate is crystallised from pentane at 0° C

Sources & evidence

ORD record
ord-e44ff1569e044277b06bdc606440438d
Source dataset
uspto-grants-1978_09
Patent number
US04115416

Reaction notes

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