Methanol → 2H-1-Benzopyran-6-ol, 3,4-dihydro-2-methoxy-2,5,7,8-tetramethyl-

HRID 1415222Notes

Reaction equation

HRID 1415222 reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].[CH:12]([C:14]([CH3:16])=[O:15])=[CH2:13].[CH3:17]O>>[OH:11][C:3]1[C:2]([CH3:1])=[C:8]2[C:6](=[C:5]([CH3:9])[C:4]=1[CH3:10])[O:7][C:14]([O:15][CH3:17])([CH3:16])[CH2:12][CH2:13]2

Participants

4

Reactant 3

HCID 887MethanolHCID 6570Methyl vinyl ketoneHCID 12785Trimethylhydroquinone

Product 1

HCID 1037632H-1-Benzopyran-6-ol, 3,4-dihydro-2-methoxy-2,5,7,8-tetramethyl-

Procedure

A solution of 304.4 g. (2.0 mol) of trimethylhydroquinone in 1.2 liters of methanol and 300 ml. of trimethyl orthoformate was degassed, placed under N2 and cooled in an ice bath to 3 degrees centigrade. To the flask was added 5.0 ml. of concentrated aqueous sulfuric acid followed, dropwise over 3.0 hours, by 340 ml. (about 4.0 mol) of methyl vinyl ketone. The suspension was stirred without cooling for 44 hours. The mixture was worked up by extracting with diethyl ether, and washing with water, and saturated aqueous sodium bicarbonate and dried over sodium sulfate. The solvent was removed on a rotary evaporator at 30° to 50° centigrade to give (±)-6-hydroxy-2-methoxy-2,5,7,8-tetramethylchroman as a light tan solid.

Workup

  1. customof trimethyl orthoformate was degassed
  2. temperaturecooled in an ice bath to 3 degrees centigrade
  3. additionTo the flask was added 5.0 ml
  4. temperaturewithout cooling for 44 hours
  5. extractionby extracting with diethyl ether
  6. washwashing with water, and saturated aqueous sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed on a rotary evaporator at 30° to 50° centigrade

Sources & evidence

ORD record
ord-0048b7458ee34c7c98cd34d8c8cba8c3
Source dataset
uspto-grants-1977_01
Patent number
US04003919

Reaction notes

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