Sodium Hydroxide → HCID 15015792, compound

HRID 728747Notes

Reaction equation

HRID 728747 reaction equation
[CH2:1]([O:8][CH:9]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH:10]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:11]([O:13]CC(C1C=CC=CC=1)=O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.CO>[CH2:1]([O:8][CH:9]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH:10]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54241444HCID 54241444, compound

Product 1

HCID 15015792HCID 15015792, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Finally, phenacyl 3-benzyloxy-2-n-tetradecyl-octadecanoate (V) (1.81 g, 2.57 millimole) was dissolved in a mixed solvent (70 ml) of tetrahydrofuran and methanol (1:1) and 1N sodium hydroxide (7.70 ml, 7.70 millimole) was added thereto, and the mixture was reacted at 65° C. for 2.5 hours. The solvent was distilled off from the reaction mixture, and water and tetrahydrofuran were added to dissolve the residue. Then the solution was acidified with 2N hydrochloric acid (to pH of about 2) with ice cooling, and extracted with ethyl acetate, and the organic phase was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off from the organic phase, the residue was dissolved in a developing solvent (n-hexane:ethyl acetate=8:2), and the obtained solution was purified over a silicagel column (n-hexane:ethyl acetate=8:2). The fast eluting fractions comprising impurities were discarded and the later colorless fractions were pooled. The solvent was evaporated off from the pooled fractions, and the residue was purified over a silicagel column (benzene:ethyl acetate=9:1) again, to give 3-benzyloxy-2-n-tetradecyl-octadecanoic acid (VI) (878 mg, yield 58%) in the form of colorless oil.

Workup

  1. additionwas added
  2. customthe mixture was reacted at 65° C. for 2.5 hours
  3. distillationThe solvent was distilled off from the reaction mixture, and water and tetrahydrofuran
  4. additionwere added
  5. dissolutionto dissolve the residue
  6. extractionextracted with ethyl acetate
  7. washthe organic phase was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off from the organic phase
  10. dissolutionthe residue was dissolved in a developing solvent (n-hexane:ethyl acetate=8:2)
  11. customthe obtained solution was purified over a silicagel column (n-hexane:ethyl acetate=8:2)
  12. washThe fast eluting fractions
  13. customThe solvent was evaporated off from the pooled fractions
  14. customthe residue was purified over a silicagel column (benzene:ethyl acetate=9:1) again

Sources & evidence

ORD record
ord-1f48717625f648639a17ca481b8dffc1
Source dataset
uspto-grants-1991_09
Patent number
US05049664

Reaction notes

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