Hydrochloric Acid → HCID 15015794, compound

HRID 728750Notes

Reaction equation

HRID 728750 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.O.Cl>O1CCCC1.CO.[OH-].[Na+]>[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][CH2:51][CH2:1][CH2:2][CH2:3][CH3:4])[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 54241444HCID 54241444, compound

Product 1

HCID 15015794HCID 15015794, compoundYield 120.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

Phenacyl 3t-(t-butyldimethyl siloxy)-2-n-tetradecyl-11icosenoate (V)(798 mg, 1.06 millimole) was dissolved in a mixed solvent of tetrahydrofuran (15.8 ml) and methanol (15.8 ml), and 1N sodium hydroxide solution (3.2 ml) was added. The reaction mixture was heated for 1.5 hours at 70° C., and water (150 ml) was added thereto. The reaction mixture was acidified with 2N hydrochloric acid (pH:about 2) and was extracted twice with ethyl acetate. The organic phase was washed with water and dried over anhydrous sodium sulfate, and the inorganic salt was filtered off, and the solvent was distilled off from the filtrate. The obtained residue was purified over a silicagel column (n-hexane:ethyl acetate=93:7) to give 3-(t-butyldimethylsilyloxy)-2- n-tetradecyl-11-icosenoic acid (VI)(410 mg, yield 60.9%) in the form of pale yellow oil.

Workup

  1. additionwas added
  2. extractionwas extracted twice with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationthe inorganic salt was filtered off
  6. distillationthe solvent was distilled off from the filtrate
  7. customThe obtained residue was purified over a silicagel column (n-hexane:ethyl acetate=93:7)

Sources & evidence

ORD record
ord-cea3892f8b9b4c5f8a1dfcd13f875159
Source dataset
uspto-grants-1991_09
Patent number
US05049664

Reaction notes

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