Sodium Hydroxide → alpha-[p-(1-Cyclohexenyl)-phenoxy]-decanoic acid

HRID 1764142Notes

Reaction equation

HRID 1764142 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=2)=[CH:17][CH:16]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])C.[OH-].[Na+]>C(O)C>[C:21]1([C:18]2[CH:17]=[CH:16][C:15]([O:14][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:4]([OH:27])=[O:3])=[CH:20][CH:19]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53893361alpha-[p-(1-Cyclohexenyl)-phenoxy]-decanoic acid ethyl ester

Product 1

HCID 20306762alpha-[p-(1-Cyclohexenyl)-phenoxy]-decanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 22.7 g of α-[p-(1cyclohexenyl)-phenoxy]-decanoic acid ethyl ester in 120 ml of ethanol are added 100 ml of 2N sodium hydroxide solution and the mixture stirred for 3 hours at room temperature. The ethanol is stripped off in vacuo and the residue partitioned between 2N hydrochloric acid and ether. The organic phase is washed until neutral, dried over sodium sulphate and evaporated to dryness. Distillation of the residue at 0.03 mm yields in the fraction boiling at 175°-180° C the α-[p-(1-cyclohexenyl)-phenoxy]-decanoic acid of the formula ##STR22## (m.p. 75°-78° C).

Workup

  1. customthe residue partitioned between 2N hydrochloric acid and ether
  2. washThe organic phase is washed until neutral,
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness
  5. distillationDistillation of the residue at 0.03 mm

Sources & evidence

ORD record
ord-d2156f8339844414a431c5c5acd29393
Source dataset
uspto-grants-1978_09
Patent number
US04115416

Reaction notes

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