Butyl bromide → HCID 20462416, compound
Reaction equation
[CH2:1]([OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[Na].[CH2:14](Br)[CH2:15][CH2:16][CH3:17]>>[CH2:14]([O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH2:15][CH2:16][CH3:17]Participants
Procedure
Monosodium decane-1,10-diol is reacted with n-butyl bromide to give oily 10-n-butoxydecanol in a yield of 62% of theory. This is brominated with phosphorus tribromide in the presence of pyridine to give an oily product in a yield of 37% of theory. After reaction of this 10-n-butoxydecyl bromide with monosodium ethylene glycol, there is obtained oily 10-n-butoxydecyloxyethanol in a yield of 36% of theory, which is reacted with phosphorus tribromide in the presence of pyridine to give oily 10-n-butoxydecyloxyethyl bromide in a yield of 52% of theory. This is then reacted with methyl β-mercaptopropionate in the presence of sodium methylate to give a yield of 49% of theory of oily methyl β-(10-n-butoxydecyloxyethylthio)-propionate, reduction of which with lithium aluminium hydride gives a yield of 90% of theory of 3-(10-n-butoxydecyloxyethylthio]-propanol; m.p, 23°-27° C.
Sources & evidence
- ORD record
- ord-ceb44055bf1f4132a439a38e4d24e2e8
- Source dataset
- uspto-grants-1984_04
- Patent number
- US04444766
Reaction notes
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