HCID 67100203, compound → HCID 86629265, compound

HRID 1868958Notes

Reaction equation

HRID 1868958 reaction equation
[O:1]1CCCO[CH:2]1[CH2:7][CH2:8][C:9]([C:11]1[C:12](=[O:26])[C:13]([CH3:25])([CH3:24])[C:14]2[C:19]([C:20]=1[OH:21])=[CH:18][C:17]([Cl:22])=[C:16]([Cl:23])[CH:15]=2)=[O:10]>C(O)(=O)C.O.O>[Cl:23][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][C:17]=1[Cl:22])[C:20]([OH:21])=[C:11]([C:9](=[O:10])[CH2:8][CH2:7][CH:2]=[O:1])[C:12](=[O:26])[C:13]2([CH3:25])[CH3:24]

Participants

4

Reactant 1

HCID 67100203HCID 67100203, compound

Product 1

HCID 86629265HCID 86629265, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3-(3-(1,3-dioxan-2-yl)propanoyl)-6,7-dichloro-4-hydroxy-1,1-dimethylnaphthalen-2(1H)-one (0.26 g, 0.65 mmol) in 25 mL acetic acid/water (4:1) was warmed to 95° C. and stirred for 1 hour. The mixture was treated with 10 mL water and stirred at 95° C. for another 30 minutes. The reaction mixture was diluted with 20 mL water and cooled to room temperature. The resulting mixture was then diluted with 200 mL additional water. The precipitate that formed was filtered and washed with 20 mL H2O. The crude precipitate was dissolved in 100 mL DCM, washed with 20 mL saturated NH4Cl, dried over anhydrous Na2SO4, and concentrated to give 0.22 g of the product as a pale yellow solid. MS m/e: 341 (M+H)+.

Workup

  1. stirringstirred at 95° C. for another 30 minutes
  2. temperaturecooled to room temperature
  3. customThe precipitate that formed
  4. filtrationwas filtered
  5. washwashed with 20 mL H2O
  6. dissolutionThe crude precipitate was dissolved in 100 mL DCM
  7. washwashed with 20 mL saturated NH4Cl
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7d6e0ee175644b5f97c5f09bf3d377d0
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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