Barium Carbonate → 2-Bromomethyl-3-hexadecyloxypropanol benzoate

HRID 847012Notes

Reaction equation

HRID 847012 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]1[CH2:24][O:23][CH:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:21][CH2:20]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][CH3:16].[Br:31]N1C(=O)CCC1=O.C(=O)([O-])[O-].[Ba+2]>ClCCl>[C:22]([O:21][CH2:20][CH:19]([CH2:24][Br:31])[CH2:18][O:17][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][CH3:16])(=[O:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10563Barium CarbonateHCID 67184N-bromobutanimideHCID 198842025-Hexadecyloxymethyl-2-phenyl-1,3-dioxane

Product 1

HCID 537978482-Bromomethyl-3-hexadecyloxypropanol benzoateYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 14.703 g (35.2 mM) of 5-n-hexadecyloxymethyl-2-phenyl-1,3-dioxane n2, 6.90 g (38.4 mM) of N-bromosuccinimide and 700 mg of barium carbonate in 200 ml of dichloromethane is heated under refluxing for 1 hour. After cooling, the mixture is poured into an ice cooled saturated aqueous sodium bicarbonate and the product is isolated by dichloromethane extraction. The dichloromethane layer is washed with 10% aqueous sodium thiosulfate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated. Purification of the residue by column silica gel chromatography using n-hexane-ethyl acetate (9:1) mixture as an eluent affords 13.843 g (79.3% yield) of the titled compound n3.

Workup

  1. temperatureis heated
  2. temperatureunder refluxing for 1 hour
  3. temperatureAfter cooling
  4. washThe dichloromethane layer is washed with 10% aqueous sodium thiosulfate and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customPurification of the residue by column silica gel chromatography

Sources & evidence

ORD record
ord-af8c2137227b41bd996cb08f9bf84ad0
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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