Myristyl bromide → HCID 10248114, compound

HRID 1461908Notes

Reaction equation

HRID 1461908 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.[CH2:13](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][CH3:26].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:26]([O:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:12])[CH:10]=[CH:9][CH:8]=1)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13]

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium Carbonate3×HCID 39129Methyl 3-Hydroxyphenylacetate

Product 1

HCID 10248114HCID 10248114, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 46.5 g of 3-hydroxybenzeneacetic acid methyl ester, 77.6 g n-tetradecyl bromide and 42.54 g of potassium carbonate in 500 ml of acetone is refluxed for 24 hours. Another 15.5 g of potassium carbonate is added and reflux continued for another 24 hours. An additional 15.5 g of potassium carbonate is added and reflux continued for another 24 hours. The mixture is filtered and the filtrate evaporated to a residue which is poured into water and extracted with ether. The organic layer is dried and evaporated to a residue which is crystallized from hexane to give 45 g of the desired product as a white solid, m.p. 31°-33° C.

Workup

  1. temperatureis refluxed for 24 hours
  2. temperaturereflux
  3. temperaturereflux
  4. waitcontinued for another 24 hours
  5. filtrationThe mixture is filtered
  6. customthe filtrate evaporated to a residue which
  7. additionis poured into water
  8. extractionextracted with ether
  9. customThe organic layer is dried
  10. customevaporated to a residue which
  11. customis crystallized from hexane

Sources & evidence

ORD record
ord-2fb5cfbafd39490ab75c05aba7cf479c
Source dataset
uspto-grants-1991_12
Patent number
US05077409

Reaction notes

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