Acetic Acid → 6-Cyano-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid

HRID 2251594Notes

Reaction equation

HRID 2251594 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:24]([O:26]C)=[O:25])[C:6]2[O:10][C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8][C:7]=2[CH:23]=1)#[N:2].O[Li].O.CC(O)=O>CO.C(Cl)Cl.O>[C:1]([C:3]1[CH:4]=[C:5]([C:24]([OH:26])=[O:25])[C:6]2[O:10][C:9]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:8][C:7]=2[CH:23]=1)#[N:2]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 69222600Methyl 6-cyano-2,2-diphenyl-1,3-benzodioxole-4-carboxylate

Product 1

HCID 692224266-Cyano-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 6-cyano-2,2-diphenyl-1,3-benzodioxole-4-carboxylate (60 mg, 0.168 mmol, 1 eq.) in a mixture of 3 mL MeOH and 0.5 mL CH2Cl2, a solution of LiOH.H2O (21 mg, 0.5 mmol, 3 eq.) in 3 mL H2O was added. The reaction mixture was vigorously stirred 16 h at r.t., then acidified with 10% AcOH in H2O and extracted with EtOAc (3×20 mL). The combined organic phases were washed with saturated aqueous NaCl solution, dried over MgSO4, and the solvents evaporated under reduced pressure to yield the desired compound as a colorless solid.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organic phases were washed with saturated aqueous NaCl solution
  3. dry with materialdried over MgSO4
  4. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-6c64b8cb4f2c42b89d4c8dda5506fb17
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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