Citric Acid → HCID 7671523, compound

HRID 864502Notes

Reaction equation

HRID 864502 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)#[N:2].[OH:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:11][C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 7671523HCID 7671523, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-cyanobenzyl bromide (40 mmol, 7.84 g), methyl 3-hydroxybenzoate (40 mmol, 6.08 g) and potassium carbonate (60 mmol, 8.29 g) in 50 mL DMF was stirred at 60° C. overnight and the solution was cooled to room temperature. To it was added dilute citric acid followed by ethyl acetate. The organic layer was separated, washed with brine, NaHCO3 and brine, dried (MgSO4), and concentrated to give a solid. The solid was washed with ether two times to give 6.2 g (60%) product. NMR (DMSO-d6): δ7.88 (d, 2H); 7.66 (d, 2H); 7.58 (m, 2H); 7.46 (t, 1H); 7.32 (dd, 1H); 5.30 (s, 2H); 3.84 (s, 3H).

Workup

  1. temperaturethe solution was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with brine, NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a solid
  7. washThe solid was washed with ether two times

Sources & evidence

ORD record
ord-6c2f899acb704ab0bbfb7a7f0670ecfd
Source dataset
uspto-grants-1996_10
Patent number
US05563158

Reaction notes

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