Sodium Hydroxide → 2-Hydroxy-4-octadecenoic acid

HRID 483881Notes

Reaction equation

HRID 483881 reaction equation
[OH:1][CH:2]([CH2:7][CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:3]([O:5]C)=[O:4].[OH-].[Na+]>O.CO>[OH:1][CH:2]([CH2:7][CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54429174Methyl 2-hydroxy-4-octadecenoate

Product 1

HCID 540723342-Hydroxy-4-octadecenoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 2-hydroxy-4-octadecenoate (8.21 g, 0.026 mol, 1.0 eq) is heated under reflux with a large excess of sodium hydroxide (8.4 g, 0.21 mol, 8.1 eq) in water (20 ml) and methanol (20 ml) for 1 hour. After cooling down to room temperature, the mixture is washed with hexane (50 ml) and the organic phase separated. The clear aqueous layer is acidified to pH 1 with concentrated hydrochloric acid and the resultant mixture is extracted with diethylether (3×50 ml), the combined organic layers being washed with brine (50 ml) dried over anhydrous magnesium sulphate and evaporated to give a white solid. This is recrystallised from ethyl acetate/hexane to give the product acid (5) as white needles, 6.35 g (81%), mp 78-79.5° C.

Workup

  1. washthe mixture is washed with hexane (50 ml)
  2. customthe organic phase separated
  3. extractionthe resultant mixture is extracted with diethylether (3×50 ml)
  4. washthe combined organic layers being washed with brine (50 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated
  7. customto give a white solid
  8. customThis is recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-23a335bf59dd40b38b6c77105b3b0a24
Source dataset
uspto-grants-1993_07
Patent number
US05227503

Reaction notes

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