Hydrogen Peroxide → HCID 12184032, compound

HRID 522496Notes

Reaction equation

HRID 522496 reaction equation
[C:1]([O:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23](C=O)[CH:22]=1)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH-:30].[K+].OO>C(O)(C)C.O>[C:1]([O:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([OH:30])[CH:22]=1)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 118047013HCID 118047013, compound

Product 1

HCID 12184032HCID 12184032, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Conditions

Temperature
35 °C

Procedure

The aldehyde from example 2 (23.6 g, 58.5 mmole mmole) was dissolved in 100 mL of isopropyl alcohol at 45° C. The solution was cooled to 35° C. and 8.8 g of 45% KOH (70 mmoles) in 150 mL of water was dripped in at 30-35° C. The solution was cooled 20-25° C. and a solution of 8 g of 35% hydrogen peroxide (82 mmole) in 10 mL of water was dripped in over about 20 min at 20-25° C. A mild exotherm was noted, but the temperature was easily held by a water bath. The product precipitated during the addition of the peroxide. The slurry was held 1 hr at which time it exhibited a weak peroxide test (starch-iodide paper). Acetic acid (2mL) was added to reduce the pH from ca. 8 to ca. 6. The slurry was filtered, washed with water, and the product was air-dried to give 20.8 g (91%) of white solid. HPLC analysis indicated an area % product of 93.6, the melting point was 61-62° C., and the H1 NMR was consistent with the structure. The composition of Example 3 prior to isolation by HPLC: 91% product, 1% formate ester 9, 3% starting material.

Workup

  1. customwas dripped in at 30-35° C
  2. temperatureThe solution was cooled 20-25° C.
  3. customwas dripped in over about 20 min at 20-25° C
  4. customthe temperature was easily held by a water bath
  5. customThe product precipitated during the addition of the peroxide
  6. additionAcetic acid (2mL) was added
  7. filtrationThe slurry was filtered
  8. washwashed with water
  9. customthe product was air-dried

Sources & evidence

ORD record
ord-c6c6b84bb77c4a6b82a615d909f7a6f6
Source dataset
uspto-grants-2016_05
Patent number
US09334229B2

Reaction notes

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