Hydrochloric Acid → HCID 21997570, compound

HRID 1977259Notes

Reaction equation

HRID 1977259 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1.[CH3:19][O-:20].[Na+].Cl>CO>[CH3:19][O:20][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 21997456HCID 21997456, compound

Product 1

HCID 21997570HCID 21997570, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of methyl 4-(6-bromo-n-hexyloxy)benzoate (186 g) in methanol (1 L) was treated with 28% sodium methoxide in methanol (340 ml) and the solution refluxed for 2 hours. After cooling, the stirred solution was adjusted to pH 2 with 1M-hydrochloric acid then extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, filtered and evaporated to give a crude oil. This oil was purified on a silica gel column (2 kg, 9:1 hexane-ethyl acetate elution) to give methyl 4-(6-methoxy-n-hexyloxy)benzoate (127 g) as an oil.

Workup

  1. temperaturethe solution refluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionthen extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a crude oil
  9. customThis oil was purified on a silica gel column (2 kg, 9:1 hexane-ethyl acetate elution)

Sources & evidence

ORD record
ord-204068cd6dd44ce880ace9fed018fc57
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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