Potassium Hydroxide → HCID 178516894, compound

HRID 2261876Notes

Reaction equation

HRID 2261876 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]3[C:15](=[O:26])[C:16]4[C:21]([C:22](=[O:25])[C:23]=3Cl)=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:27].[K+]>CO.O>[CH:18]1[CH:19]=[CH:20][C:21]2[C:22]([C:23]([OH:27])=[C:14]([C@@H:11]3[CH2:10][CH2:9][C@@H:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH2:13][CH2:12]3)[C:15](=[O:26])[C:16]=2[CH:17]=1)=[O:25]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 178516332HCID 178516332, compound2×

Product 1

HCID 178516894HCID 178516894, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

87.3 g of trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-chloro-1,4-naphthoquinone (trans-isomer of Formula IV) as obtained in Example 7 was suspended in 2619 ml methanol. 128 g potassium hydroxide was dissolved in 873 ml water and added drop-wise to the suspension under heating over a period of 20 minutes. Refluxed was extended for another 45 minutes before cooling to 0-5° C. and filtered. The filtrate was acidified with 50% aqueous hydrochloric acid to precipitate the product. The precipitated product was filtered, and recrystallized from acetonitrile to obtain 71.6 g (86% yield) atovaquone.

Workup

  1. additionadded drop-wise to the suspension
  2. temperatureunder heating over a period of 20 minutes
  3. temperatureRefluxed
  4. filtrationfiltered
  5. customto precipitate the product
  6. filtrationThe precipitated product was filtered
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-4a238b89f998496eadb46ae57b17bda4
Source dataset
uspto-grants-2010_12
Patent number
US07847127B2

Reaction notes

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