Hydrogen Peroxide → HCID 66701185, compound

HRID 1039117Notes

Reaction equation

HRID 1039117 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[C:4]([CH:14]=[O:15])[CH:3]=1.[Na].OO.Cl([O-])=[O:20].[Na+]>C(#N)C.O>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[C:4]([C:14]([OH:20])=[O:15])[CH:3]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 5360545SodiumHCID 10632006HCID 10632006, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 66701185HCID 66701185, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

9.3 g of 4-fluoro-1-methoxynaphthalene-2-carbaldehyde were dissolved in 100 ml of acetonitrile. 2.1 g sodium dihydrogenphsophate monohydrate in 10 ml of water were added, followed by the addition of 9.5 ml hydrogen peroxide (30%). 8.9 g sodium chlorite, dissolved in 20 ml water were added drop wise while maintaining an internal temperature between 5° C. and 15° C. The reaction was then allowed to come to room temp over 2.5 h. The precipitated solid was filtered with suction, and the solid was washed with water, and dried in vacuo at 40° C. to yield 9.4 g of 4-fluoro-1-methoxynaphthalene-2-carboxylic acid. The filtrate was treated with 60 ml of cold 10% aqueous sodium bisulfite solution. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine. The organic layer was washed with 0.2 N NaOH twice. The washes were acidified with 6 N HCl to pH 3, whereupon crystallization occurred. The precipitating product was filtered, washed with water and dried in vacuo at 40° C. to yield a second batch of 1.0 g of 4-fluoro-1-methoxynaphthalene-2-carboxylic acid.

Workup

  1. additionwere added drop wise
  2. temperaturewhile maintaining an internal temperature between 5° C. and 15° C
  3. filtrationThe precipitated solid was filtered with suction
  4. washthe solid was washed with water
  5. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-fd95d4e764c049ec8e018328dc1237a7
Source dataset
uspto-grants-2013_10
Patent number
US08552033B2

Reaction notes

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