Sodium Hydroxide → 3-Cyclododecylpropanoic acid

HRID 129528Notes

Reaction equation

HRID 129528 reaction equation
[CH:1]1([CH2:13][CH2:14][C:15]([O:17]C)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[CH:1]1([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 152958663-Cyclododecylpropanoic acid, methyl ester

Product 1

HCID 27291133-Cyclododecylpropanoic acidYield 25.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 7.6 g (30 mmol) of methyl 3-cyclododecylpropanoate in 100 ml of methanol is added 2.4 g of sodium hydroxide. The mixture is heated to 55° C. and is maintained for 4 hours. The reaction mixture is diluted with water and is extracted with hexane. The aqueous phase is acidified with 1N hydrochloric acid and is extracted (2 times) with ethyl ether. The combined ethereal extracts are washed with 1N hydrochloric acid and are dried over magnesium sulfate. Filtration and evaporation gives 7.48 g of crude title compound. Recrystallization of a portion of the product from hexane gives 1.81 g of the title compound: m.p. 72°-74° C.; IR (KBr) 1715 cm-1 ; NMR (CDCl3) δ 1.34 (m, 23 H), 1.57 (q, 2 H, J=8 Hz), 2.36 (t, 2 H, J=8 Hz).

Workup

  1. temperatureis maintained for 4 hours
  2. extractionis extracted with hexane
  3. extractionis extracted (2 times) with ethyl ether
  4. washThe combined ethereal extracts are washed with 1N hydrochloric acid
  5. dry with materialare dried over magnesium sulfate
  6. filtrationFiltration and evaporation
  7. customgives 7.48 g of crude title compound
  8. customRecrystallization of a portion of the product from hexane

Sources & evidence

ORD record
ord-d66753498b0240478bb4a90008b79166
Source dataset
uspto-grants-1995_11
Patent number
US05468774

Reaction notes

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