Benzyl Chloride → HCID 14877715, compound

HRID 478095Notes

Reaction equation

HRID 478095 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:50](Cl)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.CCCCCC>[CH2:50]([O:22][CH:21]([CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][OH:30])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 14373146HCID 14373146, compound

Product 1

HCID 14877715HCID 14877715, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

To 6.5 g (9.6 millimole) of 1-O-octadecyl-3-O-[2-(2-trityloxyethoxy)ethyl]glycerol synthesized in Working Example 1 were added 2.3 g (18 millimole) of benzyl chloride, 4 g (50 millimole) of 50% sodium hydroxide, and 160 mg (0.5 millimole) of cetyltrimethylammonium chloride, and the mixture was stirred at 70° C. for 18 hours. After cooling, hexane was added and the organic layer was collected by decantation. Hexane was distilled off under reduced pressure, and to the residue 50 ml of dioxane, 8 ml of 2N hydrochloric acid and 20 ml of methanol were added, and then the resulting mixture was stirred at 75° C. for 4 hours. After addition of 50 ml of water, the organic solvent was distilled off under reduced pressure, and the residue was partitioned between dichloromethane and water. The organic layer was collected and dichloromethane was distilled off, and the residue was purified by silica gel column chromatography (Merck Co., Art.7734, 150 g, Eluant; hexane-ethyl acetate=6:1, hexane-ethyl acetate-acetone=6:1:1), to give 4.7 g (92%) of the above-mentioned compound.

Workup

  1. temperatureAfter cooling
  2. customthe organic layer was collected by decantation
  3. distillationHexane was distilled off under reduced pressure
  4. additionto the residue 50 ml of dioxane, 8 ml of 2N hydrochloric acid and 20 ml of methanol were added
  5. stirringthe resulting mixture was stirred at 75° C. for 4 hours
  6. additionAfter addition of 50 ml of water
  7. distillationthe organic solvent was distilled off under reduced pressure
  8. customthe residue was partitioned between dichloromethane and water
  9. customThe organic layer was collected
  10. distillationdichloromethane was distilled off
  11. customthe residue was purified by silica gel column chromatography (Merck Co., Art.7734, 150 g, Eluant; hexane-ethyl acetate=6:1, hexane-ethyl acetate-acetone=6:1:1)

Sources & evidence

ORD record
ord-e9aa83d2d5694f239ef6a127c31fa079
Source dataset
uspto-grants-1989_12
Patent number
US04889953

Reaction notes

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