Myristyl bromide → HCID 54402223, compound

HRID 247972Notes

Reaction equation

HRID 247972 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([Cl:12])[CH:6]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])=[C:7]([Cl:12])[CH:6]=1

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 92625Methyl 3-chloro-4-hydroxyphenylacetate

Product 1

HCID 54402223HCID 54402223, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 45 g of product from Example 62, 62.2 g of 1-bromotetradecane, 58.9 g of powdered potassium carbonate and 500 ml of acetone is heated at reflux temperature for 51 hours. The cooled solution is filtered and concentrated in vacuo. The residue is dissolved in methylene chloride, washed with 2% sodium bicarbonate and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:5% ethyl acetate) and recrystallized from hexane to give 76.8 g of the desired product.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 51 hours
  3. filtrationThe cooled solution is filtered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washwashed with 2% sodium bicarbonate and saturated sodium chloride
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by column chromatography (silica gel:5% ethyl acetate)
  10. customrecrystallized from hexane

Sources & evidence

ORD record
ord-1593afee4a56490bbc42645912878727
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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