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

HRID 1764140Notes

Reaction equation

HRID 1764140 reaction equation
C([O:3][C:4](=[O:28])[CH:5]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]=2)=[CH:18][CH:17]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])C.[OH-].[Na+]>C(O)C>[C:22]1([C:19]2[CH:18]=[CH:17][C:16]([O:15][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:4]([OH:28])=[O:3])=[CH:21][CH:20]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53857244alpha-[p-(1-Cyclohexenyl)-phenoxy]-undecanoic acid ethyl ester

Product 1

HCID 20306753alpha-[p-(1-Cyclohexenyl)-phenoxy]-undecanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 27 g of α-[p-(1-cyclohexenyl)-phenoxy]-undecanoic acid ethyl ester in 150 ml of ethanol are added 100 ml of 2N sodium hydroxide solution and the mixture stirred for 2 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 0.04 mm yields in the fraction boiling at 185°-190° C the α-[p-(1-cyclohexenyl)-phenoxy]-undecanoic acid of the formula ##STR20## (m.P. 70°-73° 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 0.04 mm

Sources & evidence

ORD record
ord-6291f296f7d54b3fae4347de8aa7cc14
Source dataset
uspto-grants-1978_09
Patent number
US04115416

Reaction notes

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