Potassium Carbonate → HCID 67308753, compound

HRID 240304Notes

Reaction equation

HRID 240304 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][C:17](=[O:34])[CH:18](Br)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:17]([O:16][CH3:15])=[O:34])[CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13382081tert-Butyl 3-hydroxybenzoateHCID 13706912Methyl 2-bromohexadecanoate

Product 1

HCID 67308753HCID 67308753, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

3-Hydroxy-benzoic acid tert-butyl ester (1.79 g) was dissolved in MeCN 75 ml, then bromo-hexadecanoic acid methyl ester (3.22 g) was added followed by K2CO3 (2.5 g). The reaction was stirred for 3 d at 80° C. The reaction mixture was filtered. The filtrate was evaporated, and the residue was dissolved in EtOAc 100 ml, and the EtOAc layer was washed twice with 100 ml brine. The organic layer was dried over MgSO4 filtered and the solvent was removed by evaporation to give 4.165 g (98%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customThe filtrate was evaporated
  3. dissolutionthe residue was dissolved in EtOAc 100 ml
  4. washthe EtOAc layer was washed twice with 100 ml brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed by evaporation
  8. customto give 4.165 g (98%)

Sources & evidence

ORD record
ord-f654cb97308f4fcd975925401b1ca48c
Source dataset
uspto-grants-2014_02
Patent number
US08648041B2

Reaction notes

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