Toluene → HCID 22164641, compound

HRID 1032631Notes

Reaction equation

HRID 1032631 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]([CH2:13][OH:14])[CH2:5]1.[C:16]1(C)C=CC=CC=1.S(OC)(OC)(=O)=O>C1(C)C(C)=CC=CC=1.O>[CH3:3][C:4]1([CH3:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]([CH2:13][O:14][CH3:16])[CH2:5]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 15105986HCID 15105986, compound

Product 1

HCID 22164641HCID 22164641, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

A solution of 17.25 g (0.43 mol) of 60% sodium hydride in 500 ml of xylene was heated to 100° C. To this was dropwise added over 2 hours a mixture of 69 g (0.39 mol) of 1,1-dimethyl-3-hydroxymethylindane (IX) and 250 ml of toluene. After stirring for 5 hours, 27.1 g (0.215 mol) of dimethyl sulfate was added dropwise to the reaction mixture over 2 hours. After the addition, the mixture was stirred for 3 hours to complete the reaction. 250 ml of water was added to the resulting reaction mixture to separate the water and organic layers. The organic layer was washed with water, an aqueous solution of sodium sulfate, and saturated brine, and dried over anhydrous magnesium sulfate. After removing the solvent, the residue was distilled under reduced pressure to produce 68.3 g (0.36 mol) of 1,1-dimethyl-3-methoxymethylindane at a yield of 92%. The product was a colorless, transparent liquid having a green, herbal, woody odor.

Workup

  1. additionTo this was dropwise added over 2 hours
  2. additionAfter the addition
  3. stirringthe mixture was stirred for 3 hours
  4. customthe reaction
  5. customto separate the water and organic layers
  6. washThe organic layer was washed with water
  7. dry with materialan aqueous solution of sodium sulfate, and saturated brine, and dried over anhydrous magnesium sulfate
  8. customAfter removing the solvent
  9. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-174fdf0a3070429aa1f93df49fe85fb5
Source dataset
uspto-grants-1990_09
Patent number
US04959349

Reaction notes

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