Chloromethyl Methyl Ether → 2'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl2-butenyl)acetophenone

HRID 2254193Notes

Reaction equation

HRID 2254193 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[C:6]([OH:13])[CH:5]=[C:4]([OH:14])[C:3]=1[C:15](=[O:17])[CH3:16].C(N(CC)C(C)C)(C)C.[CH3:27][O:28][CH2:29]Cl.[O:31]1[CH2:35]CC[CH2:32]1>>[OH:1][C:2]1[C:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH2:27][O:28][CH3:29])[CH:5]=[C:4]([O:14][CH2:32][O:31][CH3:35])[C:3]=1[C:15](=[O:17])[CH3:16]

Participants

5

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 11687311Ethanone, 1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-

Product 1

HCID 110993722'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl2-butenyl)acetophenone

Procedure

Then, 30.0 g of 2',4',6'-trihydroxy-3'-(3-methyl- 2-butenyl)acetophenone was dissolved in tetrahydrofuran and 131.7 ml of N,N-diisopropylethylamine was added to the solution, and the mixture was stirred for 1 hour. Then, 48.0 ml of chloromethyl methyl ether was dropped into the mixture and the mixture was stirred for 3 hours. The mixture was extracted with dimethyl ether, and the organic layer was washed with water, dried with anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization from ethyl acetate gave 21.5 g of 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl-2-butenyl)acetophenone.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. extractionThe mixture was extracted with dimethyl ether
  3. washthe organic layer was washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-cecbc79ca79842c8ad87a23fede799d7
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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