Sulfuric Acid → HCID 66789630, compound

HRID 2191605Notes

Reaction equation

HRID 2191605 reaction equation
[CH3:1][C:2]([CH3:6])([OH:5])[C:3]#[N:4].[CH3:7][O:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:10]=1[CH:11]=O.[OH:19]S(O)(=O)=O.CC(OC(C)=O)=O>CC(O)=O.CCOC(C)=O>[CH3:18][O:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:9]([O:8][CH3:7])[C:10]=1[CH:11]1[NH:4][C:3](=[O:19])[C:2]([CH3:6])([CH3:1])[O:5]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6406Acetone CyanohydrinHCID 7918Acetic AnhydrideHCID 964042,6-Dimethoxybenzaldehyde

Product 1

HCID 66789630HCID 66789630, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

To a mixture of acetone cyanhydrin (851 mg), 2,6-dimethoxybenzaldehyde (1.58 g) in AcOH (10 mL) is added at 10° C. dropwise H2SO4 (1 mL) and Ac2O (0.5 mL). The reaction mixture is stirred at 10° C. for 40 min and then 10 min at RT. The reaction mixture is poured into cracked ice and extracted three times with ether. The combined organic extracts are washed with 10% aq. NaHCO3, dried (Na2SO4), filtered and concentrated to yield a crude oil. FC (EtOAc) gives the title compound as a brown oil (1.3 g, 52%). LC-MS: tR=0.47 min; [M+H]+=252.25.

Workup

  1. custom10 min
  2. customat RT
  3. additionThe reaction mixture is poured into cracked ice
  4. extractionextracted three times with ether
  5. washThe combined organic extracts are washed with 10% aq. NaHCO3
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a crude oil

Sources & evidence

ORD record
ord-358b61962e2c46d28a8c5d93852cb228
Source dataset
uspto-grants-2012_12
Patent number
US08329706B2

Reaction notes

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