Dimethyl Sulfate → 3-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4,6-dimethoxybenzaldehyde

HRID 1057840Notes

Reaction equation

HRID 1057840 reaction equation
[CH3:1][C:2]1[C:3]([C:16]2[CH:17]=[C:18]([C:21]([OH:26])=[CH:22][C:23]=2[O:24][CH3:25])[CH:19]=[O:20])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[CH3:27]OS(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[C:3]([C:16]2[CH:17]=[C:18]([C:21]([O:26][CH3:27])=[CH:22][C:23]=2[O:24][CH3:25])[CH:19]=[O:20])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 222683753-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxy-6-hydroxybenzaldehyde

Product 1

HCID 222683543-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4,6-dimethoxybenzaldehydeYield 97.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxy-6-hydroxybenzaldehyde (1.04 g, 2.95 mmol) in acetone (20 mL) was added dimethylsulfate (0.37 mL, 3.84 mmol) and potassium carbonate (490 mg, 3.55 mmol). The reaction mixture was stirred at room temperature for 15 hours and extracted with ethyl acetate (2×50 mL). The organic extracts were successively washed with water (100 mL) and a saturated aqueous solution of NaCl (100 mL), dried over MgSO4 and filtered. Removal of the solvent under reduced pressure gave 3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4,6-dimethoxybenzaldehyde (1.05 g, 97%).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe organic extracts were successively washed with water (100 mL)
  3. dry with materiala saturated aqueous solution of NaCl (100 mL), dried over MgSO4
  4. filtrationfiltered
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-5b1aa50c197348e98b63fb1223e115b9
Source dataset
uspto-grants-2003_02
Patent number
US06515003B1

Reaction notes

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