Sodium Acetate → 3,7,11,15,19,23,27,31,35,39,43-Undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl acetate

HRID 46953Notes

Reaction equation

HRID 46953 reaction equation
[CH3:1][C:2]([CH3:56])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:55])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:54])=[CH:11]/[CH2:12][CH2:13]/[C:14](/[CH3:53])=[CH:15]/[CH2:16][CH2:17]/[C:18](/[CH3:52])=[CH:19]/[CH2:20][CH2:21]/[C:22](/[CH3:51])=[CH:23]/[CH2:24][CH2:25]/[C:26](/[CH3:50])=[CH:27]/[CH2:28][CH2:29]/[C:30](/[CH3:49])=[CH:31]/[CH2:32][CH2:33]/[C:34](/[CH3:48])=[CH:35]/[CH2:36][CH2:37]/[C:38](/[CH3:47])=[CH:39]/[CH2:40][CH2:41]/[C:42](/[CH3:46])=[CH:43]/[CH2:44][OH:45].[C:57]([O-])(=[O:59])[CH3:58].[Na+]>C(OC(=O)C)(=O)C.O>[C:57]([O:45][CH2:44][CH:43]=[C:42]([CH3:46])[CH2:41][CH2:40][CH:39]=[C:38]([CH3:47])[CH2:37][CH2:36][CH:35]=[C:34]([CH3:48])[CH2:33][CH2:32][CH:31]=[C:30]([CH3:49])[CH2:29][CH2:28][CH:27]=[C:26]([CH3:50])[CH2:25][CH2:24][CH:23]=[C:22]([CH3:51])[CH2:21][CH2:20][CH:19]=[C:18]([CH3:52])[CH2:17][CH2:16][CH:15]=[C:14]([CH3:53])[CH2:13][CH2:12][CH:11]=[C:10]([CH3:54])[CH2:9][CH2:8][CH:7]=[C:6]([CH3:55])[CH2:5][CH2:4][CH:3]=[C:2]([CH3:56])[CH3:1])(=[O:59])[CH3:58]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 528047415575-14-1

Product 1

HCID 30538473,7,11,15,19,23,27,31,35,39,43-Undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent2×

Conditions

Temperature
100 °C

Procedure

3.5 Grams of undecaprenol were dissolved in 15 ml of acetic acid anhydride and the solution was added with 2.0 g of anhydrous sodium acetate at room temperature. The mixture was stirred at 100° C. for one hour to complete the reaction. Upon cooling, the reaction product was poured in water to hydrolyze excessive acetic acid anhydride. After extraction with n-hexane, the extract was washed with water and concentrated. The concentrate was purified by chromatography with 50 g of silica gel in n-hexane/benzene solvent mixture as elution solvent to obtain the final product as white solid (m.p. 36.0°-37.0° C.). Yield 3.5 g.______________________________________Elementary analysis as C57H92O2 : C H______________________________________Theoretical (%): 84.59 11.46Found (%): 84.61 11.46______________________________________

Workup

  1. customthe reaction
  2. temperatureUpon cooling
  3. extractionAfter extraction with n-hexane
  4. washthe extract was washed with water
  5. concentrationconcentrated
  6. customThe concentrate was purified by chromatography with 50 g of silica gel in n-hexane/benzene solvent mixture as elution solvent

Sources & evidence

ORD record
ord-1918e4dd231046f4b0ed8ea09c877480
Source dataset
uspto-grants-1979_11
Patent number
US04175139

Reaction notes

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