Water → HCID 178516332, compound

HRID 2261875Notes

Reaction equation

HRID 2261875 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([C:14]3(Cl)[CH:23]([Cl:24])[C:22](=[O:25])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]3=[O:26])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][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]=3[Cl:24])=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 251646042-[4-(4-Chlorophenyl)cyclohexyl]-2,3-dichloro-2,3-dihydro-1,4-naphthoquinone2×

Product 1

HCID 178516332HCID 178516332, compoundYield 89.34%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

115.8 g of 2-[4-(4-chlorophenyl)cyclohexyl]-2,3-dichloro-2,3-dihydro-1,4-naphthoquinone (Formula III) obtained in Example 6 was suspended in glacial acetic acid (926 ml). 33.77 g anhydrous sodium acetate was then added to the mixture and heated to reflux for 1 hour. After which, the mixture was cooled. Water was then added. The precipitated product was filtered of and recrystallized from acetonitrile to obtain 94.5 g (89.34% yield) of the trans-isomer of the compound of Formula IV.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter which, the mixture was cooled
  4. filtrationThe precipitated product was filtered of and
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-be926c877c1f4f8e965c21610f7a81db
Source dataset
uspto-grants-2010_12
Patent number
US07847127B2

Reaction notes

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