1-Heptanol, 7-bromo- → 7-Methoxy-1-heptanol
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[CH3:10][O-:11].[Na+]>CO>[CH3:10][O:11][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 7-bromo-1-heptanol (25 g) and sodiummethoxide, 28% solution in methanol (37 ml) in methanol (250 ml) was stirred for 7 hours at 90° C. After being cooled to room temperature, the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (100:1→25:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 7-methoxy-1-heptanol (18.2 g).
Workup
- temperatureAfter being cooled to room temperature
- customthe solvent was evaporated in vacuo
- customThe residue was purified by column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (100:1→25:1)
- additionThe eluted fractions containing the desired product
- customwere collected
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-41df16ddb50f4e7a9756bd2ed6a28400
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06884774B2
Reaction notes
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