Dimethyl Sulfoxide → (+/-)-6-Benzyloxy-2-methoxy-2,5,7,8-tetramethylchroman

HRID 1415242Notes

Reaction equation

HRID 1415242 reaction equation
[OH:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([O:15][CH3:16])([CH3:14])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O>[CH2:28]([O:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([O:15][CH3:16])([CH3:14])[CH2:6][CH2:5]2)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 1037632H-1-Benzopyran-6-ol, 3,4-dihydro-2-methoxy-2,5,7,8-tetramethyl-

Product 1

HCID 14415660(+/-)-6-Benzyloxy-2-methoxy-2,5,7,8-tetramethylchroman

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 70.8 g. of (±)-6-hydroxy-2-methoxy-2,5,7,8-tetramethylchroman, 90.9 g. of anhydrous potassium carbonate, 300 ml. of dimethylsulfoxide and 69 ml. of benzyl chloride was stirred at 23° under N2 for 24 hours. The suspension was poured into water and extracted with ether. The ether solutions were washed with brine, dried over sodium sulfate and stripped of solvent to give (±)-6-benzyloxy-2-methoxy-2,5,7,8-tetramethylchroman as an oil which solidified to a light yellow mass, m.p. 70°-72.5°.

Workup

  1. additionA mixture of 70.8 g
  2. extractionextracted with ether
  3. washThe ether solutions were washed with brine
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-fcdb3336aa2b4696b59a9d79988d4f90
Source dataset
uspto-grants-1977_01
Patent number
US04003919

Reaction notes

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