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

HRID 2399064Notes

Reaction equation

HRID 2399064 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-f6dc6915798c4aa0a2ad7a40b0efc1c1
Source dataset
uspto-grants-1977_05
Patent number
US04026907

Reaction notes

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