Sodium Methoxide → HCID 22494732, compound

HRID 1816681Notes

Reaction equation

HRID 1816681 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.[CH3:20][O-:21].[Na+]>CO>[CH3:20][O:21][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 22494693HCID 22494693, compound

Product 1

HCID 22494732HCID 22494732, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of methyl 4-[7-bromo-n-heptyloxy)benzoate (2.3 g) in methanol (50 ml) and a solution of 28% sodium methoxide in methanol (3.5 ml) was refluxed for 12 hours with stirring. The reaction mixture was concentrated under reduced pressure and water was added to the residue and adjusted to pH 1 using hydrochloric acid. The precipitates were collected by filtration, washed with water and dried in vacuo to give an oil. The oil was subjected to column chromatography on silica gel (silica gel 60 F254, Merck: 100 g) and eluted with a mixture of ethyl acetate and n-hexane (1:5). The fractions containing the objective compound were combined and concentrated under reduced pressure to give methyl 4-(7-methoxyheptyloxy)benzoate (1.6 g) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customto give an oil
  7. washeluted with a mixture of ethyl acetate and n-hexane (1:5)
  8. additionThe fractions containing the objective compound
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-195d9a2f42d640d08491c52df3b94186
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

Loading…