Sodium Hydroxide → alpha-[p-(1-Cycloheptenyl)-phenoxy]-undecanoic acid

HRID 1764146Notes

Reaction equation

HRID 1764146 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:31])[CH:7]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=2)=[CH:20][CH:19]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])C>C(O)C>[C:24]1([C:21]2[CH:20]=[CH:19][C:18]([O:17][CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:6]([OH:31])=[O:5])=[CH:23][CH:22]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53939343alpha-[p-(1-Cycloheptenyl)-phenoxy]-undecanoic acid ethyl ester

Product 1

HCID 20306766alpha-[p-(1-Cycloheptenyl)-phenoxy]-undecanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 ml of 2N sodium hydroxide solution are added to 27 g of α-[p-(1-cycloheptenyl)-phenoxy]-undecanoic acid ethyl ester in 150 ml of ethanol and the mixture is stirred for 2 hours at room temperature. The ethanol is removed in vacuo and the residue is partitioned between 2 N hydrochloric acid and ether. The organic phases are washed until neutral, dried over sodium sulphate and concentrated by evaporation in vacuo. Distillation of the residue at 0.04 mm gives α-[p-(1-cycloheptenyl)-phenoxy]-undecanoic acid, of melting point 79°-81° C (from n-hexane), in the fraction boiling at 185°-190° C.

Workup

  1. customThe ethanol is removed in vacuo
  2. customthe residue is partitioned between 2 N hydrochloric acid and ether
  3. washThe organic phases are washed until neutral,
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. distillationDistillation of the residue at 0.04 mm

Sources & evidence

ORD record
ord-88fb670da81f46b69b71367c23185e95
Source dataset
uspto-grants-1978_09
Patent number
US04115416

Reaction notes

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