Cesium carbonate → Dimethyl 5-butoxyisophthalate

HRID 58975Notes

Reaction equation

HRID 58975 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:23][CH2:24][CH2:25][CH3:26]>CC#N>[CH2:23]([O:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=1)[C:12]([O:14][CH3:15])=[O:13])[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 10962Butyl iodideHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 18667930Dimethyl 5-butoxyisophthalate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 5-hydroxyisophthalate (0.40 g, 1.90 mmol), cesium carbonate (1.30 g, 3.80 mmol) and CH3CN (12 mL) were added to a round-bottom flask and stirred for 15-30 min. iodobutane (0.42 g, 2.28 mmol) was added, and the reaction was stirred for 16 h. The solvent was concentrated under reduced pressure, and the reaction mixture was partitioned between EtOAc (50 mL) and H2O (50 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (50 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the desired product which was used without further purification.

Workup

  1. additionwas added
  2. concentrationThe solvent was concentrated under reduced pressure
  3. customthe reaction mixture was partitioned between EtOAc (50 mL) and H2O (50 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with EtOAc (50 mL)
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a61dfbe360d40bc9027ec867de0e0e5
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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