Hydrochloric Acid → HCID 21107232, compound

HRID 2377498Notes

Reaction equation

HRID 2377498 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=[O:14])[CH2:8][CH2:7][C:6]2([CH3:16])[CH3:15].[C-]#N.[Na+].C#N.Cl>CS(C)=O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=[O:14])[CH2:8][CH2:7][C:6]2([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 768Hydrogen CyanideHCID 8929Sodium CyanideHCID 22218197HCID 22218197, compound

Product 1

HCID 21107232HCID 21107232, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 6-methoxy-4,4,7-trimethyl-3,4-dihydro-2H-naphthalen-1-one (described in U.S. 2003/0166932, published Sep. 4, 2003, incorporated herein by reference; 5.5 g, 25.6 mmol) and sodium cyanide (6.25 g, 127 mmol) in anhydrous dimethylsulfoxide (100 mL) was heated at 230° C. for 48 h under argon. The reaction mixture was then cooled to ambient temperature, poured into ice and acidified (Caution! Hydrogen cyanide evolution!) with dilute hydrochloric acid and extracted with ethyl acetate (×2). The combined organic extract was washed with brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound, which was used as such for the next step (5.2 g, 100%).

Workup

  1. additionpoured into ice
  2. extractionextracted with ethyl acetate (×2)
  3. extractionThe combined organic extract
  4. washwas washed with brine (×1)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e4ab91558bdd4e7eb83256423f10dfd8
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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