Water → 3-Hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 856946Notes

Reaction equation

HRID 856946 reaction equation
[CH:1]1[C:10]2CCCC[C:5]=2C=C[C:2]=1[OH:11].O.Cl[C:14]1[C:15](=O)[C:16](C#N)=[C:17]([C:22]#[N:23])[C:18](=[O:21])[C:19]=1Cl>O1CCOCC1>[OH:21][C:18]1[C:17]([C:22]#[N:23])=[CH:16][C:15]2[C:2](=[O:11])[CH2:1][CH2:10][CH2:5][C:14]=2[CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 143055,6,7,8-Tetrahydro-2-naphthol

Product 1

HCID 218649643-Hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrileYield 40%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5,6,7,8-tetrahydro-2-naphthalenol prepared in method II-2 (1.5 g, 8.7 mmol) was dissolved in 1,4-dioxane (8 mL) in a 100 mL round bottom flask. To this was added water (2 mL), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (4.1 g, 18.2 mmol, 2.1 eq) in anhydrous 1,4-dioxane (16 mL) dropwise. The reaction mixture turned to black immediately after addition and resulting mixture was stirred at room temperature for 3 h. The mixture was filtered and the filtrate was evaporated in vacuo. The residue was participated between EtOAc and saturated aqueous sodium bicarbonate. The aqueous layer was acidified to about pH 3 and was extracted with EtOAc three times. The organic layers were combined and evaporated in vacuo. Purification using MPLC chromatography (Biotage) gave 0.64 g (40%) of 3-hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile as a light brown solid.

Workup

  1. additionafter addition
  2. customresulting mixture
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. extractionwas extracted with EtOAc three times
  6. customevaporated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-461f0709edcb44938e20f19979f597a7
Source dataset
uspto-grants-2006_12
Patent number
US07144885B2

Reaction notes

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