Dimethyl Sulfate → 3-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4,6-dimethoxybenzaldehyde
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- extractionextracted with ethyl acetate (2×50 mL)
- washThe organic extracts were successively washed with water (100 mL)
- dry with materiala saturated aqueous solution of NaCl (100 mL), dried over MgSO4
- filtrationfiltered
- customRemoval of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-4e934cac9d3b4f8bbb77adedc8d7c4cf
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07226940B2
Reaction notes
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