Diazald → 5-Chloro-2,3-dihydro-1-benzofuran-3-one

HRID 330291Notes

Reaction equation

HRID 330291 reaction equation
[N+](=C)=[N-].CN(N=O)S(C1C=CC(C)=CC=1)(=O)=O.[OH-].[K+].[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:30][CH3:31])=[C:25]([CH:29]=1)[C:26](Cl)=[O:27]>CCOCC.O.C(O)C>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[O:30][CH2:31][C:26](=[O:27])[C:25]=2[CH:29]=1

Participants

8

Reactant 4

HCID 6628Diazald2×HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 123841765-Chloro-2-methoxybenzoyl chloride

Product 1

HCID 37113525-Chloro-2,3-dihydro-1-benzofuran-3-oneYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

According to the procedure of M. E. Jung et al., J. Org. Chem., 53, 423 (1988), a solution of diazomethane in ether [prepared from N-methyl-N-nitroso-p-toluenesulfonamide (5.8 g, 0.026 mol) and potassium hydroxide (2.9 g, 0.052 mol) in H2O (7 mL), ethanol (10 mL), and ether (70 mL) utilizing a mini-Diazald® apparatus] was added to 5-chloro-2-methoxybenzoyl chloride (2.0 g, 0.010 mol). The resulting mixture was stirred for 30 minutes, concentrated, and acetic acid (20 mL) was added. After 15 minutes, the mixture was concentrated to give 1.6 g (97%) of the product as an orange solid.

Workup

  1. concentrationconcentrated
  2. additionacetic acid (20 mL) was added
  3. waitAfter 15 minutes
  4. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-f6b48cff53914792905232cfe1a9bf29
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

Loading…