Reaction equation
[CH3:1][C:2](O)([CH2:5][CH2:6][CH:7]=[C:8]([CH3:13])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH:3]=[CH2:4].N1C=CC=CC=1.P(Br)(Br)[Br:22]>CCCCCC>[Br:22][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:13])[CH2:9][CH:10]([CH3:12])[CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
19.8 g. of 3,7,9-trimethyl-1,6-decadien-3-ol, 100 ml. of hexane and 1 ml. of pyridine and cooled to -15° C. and treated dropwise over a period of 1.5 hours with a solution of 4 ml. of phosphorus tribromide in 50 ml. of hexane while maintaining the temperature between -15° and -10° C. The mixture is stirred for a further 90 minutes while slowly warming to room temperature. For the working-up, the mixture is poured on to 50 ml. of ice-water, the organic phase is separated and washed once with 20 ml. of 10% soda solution, once with 50 ml. of semi-saturated aqueous sodium chloride solution and once with 50 ml. saturated sodium chloride solution, dried over sodium sulphate and evaporated under reduced pressure. There is obtained 1-bromo-3,7,9-trimethyl-2,6-decadiene.
Workup
- additiontreated dropwise over a period of 1.5 hours with a solution of 4 ml
- additionthe mixture is poured on to 50 ml
- customof ice-water, the organic phase is separated
- washwashed once with 20 ml
- dry with materialsaturated sodium chloride solution, dried over sodium sulphate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-d4632101ccdb464f9dd9c1678292ae2e
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04011335
Linked notes
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