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Myristyl bromide → 4-Methoxy-3-(tetradecyloxy)benzoic acid methyl ester

HRID 247950
Notes
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Reaction equation

HRID 247950 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([OH:12])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>[I-].[Na+].CC(=O)CC>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH3:21])[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 536393154-Methoxy-3-(tetradecyloxy)benzoic acid methyl esterYield 71%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalyst
HCID 6569
Methyl Ethyl Ketone
Solvent

Procedure

A mixture of 45 g of product from Example 40, 51.2 g of finely powdered potassium carbonate, 72 g of 1-bromotetradecane, 1.9 g of sodium iodide and 500 ml of 2-butanone is heated at reflux temperature for 18 hours under an atmosphere of argon. The reaction is cooled and filtered. The filtrate is concentrated in vacuo and the residue is dissolved in chloroform. The organic layer is washed with 1N sodium hydroxide and saturated sodium chloride, dried and concentrated in vacuo. The residue is recrystallized from hexane to give 66.4 g of the desired product as white crystals.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 18 hours under an atmosphere of argon
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  6. dissolutionthe residue is dissolved in chloroform
  7. washThe organic layer is washed with 1N sodium hydroxide and saturated sodium chloride
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-a08e7576ffcc42b8ba5150c6dd881dbe
Source dataset
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05208247

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes