1-Heptanol, 7-bromo- → 7-Methoxy-1-heptanol

HRID 1816343Notes

Reaction equation

HRID 1816343 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

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

  1. temperatureAfter being cooled to room temperature
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (100:1→25:1)
  4. additionThe eluted fractions containing the desired product
  5. customwere collected
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-41df16ddb50f4e7a9756bd2ed6a28400
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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