Acetonitrile → HCID 58079459, compound

HRID 444992Notes

Reaction equation

HRID 444992 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[C:16]([O:20][C:21](=[O:37])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br)([CH3:19])([CH3:18])[CH3:17].C([O-])([O-])=O.[K+].[K+].C(#N)C>CCCCCCC.CCOC(C)=O>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:12]([O:14][CH2:35][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][C:21]([O:20][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:37])[CH:13]=[C:4]([C:3]([O:2][CH3:1])=[O:15])[CH:5]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl esterHCID 58079429HCID 58079429, compound

Product 1

HCID 58079459HCID 58079459, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

5-Hydroxy-isophthalic acid dimethyl ester (420 mg, 2 mmol), 15-bromo-pentadecanoic acid tert-butyl ester (755 mg, 2 mmol) and K2CO3 (415 mg, 3 mmol) were placed in a flask with acetonitrile (25 ml) and refluxed under N2. The reaction was followed by TLC (4:1 heptane/AcOEt), which indicated reaction completion after 6 h. The sample was concentrated to near dryness. AcOEt (50 ml) and water (25 ml) were added to the residue. The phases were separated and the organic phase was washed with water and brine (25 ml each), dried over MgSO4 and concentrated to yield a white crystalline solid (1.0 g, 100%).

Workup

  1. temperaturerefluxed under N2
  2. customreaction completion after 6 h
  3. concentrationThe sample was concentrated
  4. additionAcOEt (50 ml) and water (25 ml) were added to the residue
  5. customThe phases were separated
  6. washthe organic phase was washed with water and brine (25 ml each)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2ac38b540b7847bfab8389a7a3bb1c02
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Reaction notes

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