Myristyl bromide → HCID 53824641, compound

HRID 247945Notes

Reaction equation

HRID 247945 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([Cl:11])[CH:5]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])=[C:6]([Cl:11])[CH:5]=1

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 53824641HCID 53824641, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 100.0 g of 3-chloro-4-(hydroxy)benzoic acid methyl ester, 148.6 g of 1-bromotetradecane, 170.4 g of potassium carbonate and 1 L of acetone is heated at reflux temperature for 40.5 hours. The cooled reaction is filtered, concentrated in vacuo and purified by column chromatography (silica gel:0-2% ethyl acetate/hexane) to give 197.1 g of the desired product as colorless crystals.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 40.5 hours
  3. customThe cooled reaction
  4. filtrationis filtered
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (silica gel:0-2% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8b6273f2848f4ae08442ccd08bcd2c7e
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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