Citric Acid → HCID 28996603, compound

HRID 1747029Notes

Reaction equation

HRID 1747029 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.C1COCC1.[CH3:16][C:17]([CH3:20])([O-:19])[CH3:18].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[C:17]([O:19][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1)([CH3:20])([CH3:18])[CH3:16]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 792226-Chloronicotinic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 28996603HCID 28996603, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3.0 g of 6-chloronicotinic acid and 111 ml of THF was added 6.4 g of potassium tert-butoxide, followed by heating under reflux for 1 day. The reaction solution was poured into water, neutralized with citric acid, and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 2.16 g of 6-tert-butoxynicotinic acid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 day
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4d91139743d425db9c6c8f469dae2c2
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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