Sodium Hydroxide → HCID 53929976, compound

HRID 1764134Notes

Reaction equation

HRID 1764134 reaction equation
C([O:3][C:4](=[O:31])[CH:5]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=2)=[CH:19][CH:18]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])C.[OH-].[Na+]>C(O)C>[C:23]1([C:20]2[CH:19]=[CH:18][C:17]([O:16][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:4]([OH:31])=[O:3])=[CH:22][CH:21]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53699764HCID 53699764, compound

Product 1

HCID 53929976HCID 53929976, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 38 g of α-[p-(1-cyclooctenyl)-phenoxy]-dodecanoic acid ethyl ester in 150 ml of ethanol are added 150 ml of 2N sodium hydroxide solution and the mixture is stirred for 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 phases are washed until neutral, dried over sodium sulphate and evaporated to dryness in vacuo. The residue is distilled under a high vacuum at 0.05 mm and 235°-239° C. The distillate is cyrstallised from pentane to yield the α-[p-(1-cyclooctenyl)-phenoxy]-dodecanoic acid of the formula ##STR14## which melts at 45°-48° 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 phases are washed until neutral,
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness in vacuo
  6. distillationThe residue is distilled under a high vacuum at 0.05 mm and 235°-239° C

Sources & evidence

ORD record
ord-04ee762560ef4d068e8725b7a2b6802e
Source dataset
uspto-grants-1978_09
Patent number
US04115416

Reaction notes

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