Potassium hydroxy sulfite → HCID 178429091, compound

HRID 1868959Notes

Reaction equation

HRID 1868959 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[C:8]([OH:13])=[C:7]([C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[O:18])[C:6](=[O:20])[C:5]2([CH3:22])[CH3:21].[OH:23]OS([O-])=O.[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[C:8](=[O:13])[C:7]([C:14](=[O:19])[CH2:15][CH2:16][C:17]([OH:23])=[O:18])=[C:6]([OH:20])[C:5]2([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 86629265HCID 86629265, compound

Product 1

HCID 178429091HCID 178429091, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(6,7-dichloro-1-hydroxy-4,4-dimethyl-3-oxo-3,4-dihydronaphthalen-2-yl)-4-oxobutanal (0.22 g, 0.64 mmol) in 6 mL DMF was stirred at room temperature and treated with oxone (0.36 mL, 0.64 mmol). The mixture was stirred at room temperature for 2 hours. The mixture was quenched with 50 mL H2O and adjusted to pH=5 with concentrated HCl. The solid was collected by filtration and washed with 20 mL H2O. The crude was dried under high vacuum to give 0.23 g white solid. MS m/e: 357 (M+H)+. Calculated for C16H14Cl2O5: 356.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. customThe mixture was quenched with 50 mL H2O
  3. filtrationThe solid was collected by filtration
  4. washwashed with 20 mL H2O
  5. customThe crude was dried under high vacuum

Sources & evidence

ORD record
ord-3fbf1d15176945bfba66c9d401a9455b
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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