Hydrochloric Acid → HCID 54462871, compound

HRID 2254659Notes

Reaction equation

HRID 2254659 reaction equation
[CH3:1][C:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:22])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:3][C:4]([OH:6])=[O:5].CS(Cl)(=O)=O.CC1(C)[O:33][CH:32]([CH2:34]O)[CH2:31][O:30]1.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(#N)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][C:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:22])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:3][C:4]([O:6][CH2:34][CH:32]([CH2:31][OH:30])[OH:33])=[O:5]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 7528SolketalHCID 31297Methanesulfonyl chlorideHCID 134564CID 134564

Product 1

HCID 54462871HCID 54462871, compoundYield 96.9%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-50 °C

Procedure

A solution of 5.0 g of 3,7,11,15-tetramethyl-2-hexadecenoic acid and 4.3 g of 4-(N,N-dimethylamino)pyridine dissolved in 50 ml of methylene chloride was cooled to -50° C. Thereinto was dropped 1.8 g of methanesulfonyl chloride. After the completion of the dropping, the resulting mixture was stirred at the same temperature for 1 hour. Thereinto was dropped 3.2 g of 2,2-dimethyl-1,3-dioxolane-4-methanol at the same temperature. After the completion of the dropping, the temperature of the reaction mixture was elevated to room temperature in 6 hours. After the completion of the reaction, the reaction mixture was washed with 1N hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order, and the solvent was removed by distillation under reduced pressure. The residue obtained was dissolved in 50 ml of acetonitrile. To the resulting solution was added 5 ml of 2N hydrochloric acid. The resulting mixture was stirred for 5 hours at room temperature. The reaction mixture was neutralized with triethylamine, and then concentrated under reduced pressure. The residue obtained was dissolved in 20 ml of ethyl acetate. The resulting solution was washed with 1N hydrochloric acid, 3% asqueous sodium hydrogencarbonate solution and water in this order and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The redsidue obtianed was purified by a column chromatography (eluant: benzene) to obtain 6.0 g (yield: 96.7%) of oily glyceryl 3,7,11,15-tetramethyl-2-hexadecenoate.

Workup

  1. waitAfter the completion of the dropping, the temperature of the reaction mixture was elevated to room temperature in 6 hours
  2. customAfter the completion of the reaction
  3. washthe reaction mixture was washed with 1N hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe residue obtained
  6. stirringThe resulting mixture was stirred for 5 hours at room temperature
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. washThe resulting solution was washed with 1N hydrochloric acid, 3% asqueous sodium hydrogencarbonate solution and water in this order
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customThe redsidue obtianed was purified by a column chromatography (eluant: benzene)

Sources & evidence

ORD record
ord-06bf8af7d69d43648187f8edacf2d547
Source dataset
uspto-grants-1993_08
Patent number
US05236950

Reaction notes

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