Methanol → HCID 21532243, compound

HRID 1657938Notes

Reaction equation

HRID 1657938 reaction equation
BrBr.[C:3]([O:6][C:7](Br)=[C:8]([Br:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=O)C.[CH3:18][OH:19]>C(Cl)(Cl)(Cl)Cl.O>[CH3:3][O:6][CH:7]([O:19][CH3:18])[CH:8]([Br:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 887MethanolHCID 24408Bromine3×HCID 53788056HCID 53788056, compound

Product 1

HCID 21532243HCID 21532243, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

The oil is mixed with 200 ml of carbon tetrachloride and cooled in an ice bath. Bromine, diluted with an equal volume of carbon tetrachloride, is added slowly with agitation while maintaining the temperature below 10°C. Bromine addition is stopped when the bromine is no longer decolorized. To the brominated mixture, containing 1,2-dibromononen-1-yl acetate, is added 500 ml of methyl alcohol with shaking and cooling. The mixture is allowed to stand two days with occasional shaking and then diluted with 1.5 liters of water. The separated oil is washed with 5% sodium carbonate solution until free of acid and then fractionally distilled in the presence of a small amount of sodium carbonate to yield 2-bromo-nonanal dimethyl acetal.

Workup

  1. temperaturecooled in an ice bath
  2. additionis added slowly with agitation
  3. temperaturewhile maintaining the temperature below 10°C
  4. temperaturecooling
  5. stirringwith occasional shaking
  6. washThe separated oil is washed with 5% sodium carbonate solution until free of acid
  7. distillationfractionally distilled in the presence of a small amount of sodium carbonate

Sources & evidence

ORD record
ord-fe9c516ae38a463ea6ad545f9f19a010
Source dataset
uspto-grants-1976_06
Patent number
US03962321

Reaction notes

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