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

HRID 328859Notes

Reaction equation

HRID 328859 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-7d5086e9509942fa93afd4ade5b1d091
Source dataset
uspto-grants-1977_04
Patent number
US04018799

Reaction notes

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