Acetic Acid → 6-methoxymethoxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid

HRID 1608506Notes

Reaction equation

HRID 1608506 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]([CH3:17])[C:5]2[O:10][C:9]([CH3:14])([C:11]([OH:13])=[O:12])[CH2:8][CH2:7][C:6]=2[C:15]=1[CH3:16].[CH3:19][O:20][CH2:21]Br.C(O)(=O)C>N1C=CC=CC=1>[CH3:19][O:20][CH2:21][O:1][C:2]1[C:3]([CH3:18])=[C:4]([CH3:17])[C:5]2[O:10][C:9]([CH3:14])([C:11]([OH:13])=[O:12])[CH2:8][CH2:7][C:6]=2[C:15]=1[CH3:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 40634TroloxHCID 83093Bromomethyl methyl ether

Product 1

HCID 200865506-methoxymethoxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

50 grams (0.2 mol) of 6-hydroxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid are dissolved in 150 cm3 of anhydrous pyridine. 16.34 cm3 (0.2 mol) of bromomethyl methyl ether are added dropwise. The mixture is stirred for 2 hours and then the solution is poured onto ice. The mixture is acidified with acetic acid and then extracted with methylene chloride. The organic phase is washed with water and dried over anhydrous sodium sulfate, then the title product is purified by passing through a column of silica gel, eluting with methylene chloride.

Workup

  1. additionthe solution is poured onto ice
  2. extractionextracted with methylene chloride
  3. washThe organic phase is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe title product is purified
  6. washeluting with methylene chloride

Sources & evidence

ORD record
ord-2275d5dcdb7b4a1b979b2779f63c64ca
Source dataset
uspto-grants-1995_03
Patent number
US05395834

Reaction notes

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