Ethanol → 9-(Ethoxymethyl)anthracene

HRID 1939128Notes

Reaction equation

HRID 1939128 reaction equation
Cl[CH2:2][C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.O.[CH2:18]([OH:20])[CH3:19]>>[CH2:18]([O:20][CH2:2][C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH3:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 962WaterHCID 323859-(Chloromethyl)anthracene

Product 1

HCID 128432009-(Ethoxymethyl)anthracene

Procedure

A solution of 9-chloromethylanthracene (5.2 g, 23 mmole) obtained in Synthesis Example 2-(1) in ethanol (700 ml) was reacted with stirring for 10 hours at room temperature, poured into H2O (700 ml), and extracted with methylene chloride (500 ml×1). The resulting organic layer was dried over anhydrous MgSO4 and evaporated. The residual crude solid (4.25 g) was recrystallized from 50% THF/H2O to give 4.02 g of 9-ethoxymethylanthracene as orange yellow crystals, mp. 74°-75° C.

Workup

  1. customwas reacted
  2. extractionextracted with methylene chloride (500 ml×1)
  3. dry with materialThe resulting organic layer was dried over anhydrous MgSO4
  4. customevaporated
  5. customThe residual crude solid (4.25 g) was recrystallized from 50% THF/H2O

Sources & evidence

ORD record
ord-8576b3b4f74646bcbbda171e97be9fcf
Source dataset
uspto-grants-1997_12
Patent number
US05695910

Reaction notes

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