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Ethanol → 9,10-Bis(2-chloroethoxy)-2-methylanthracene

HRID 904646
Notes
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Reaction equation

HRID 904646 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[OH-].[Na+].[CH2:20](O)[CH3:21].[Cl:23][CH2:24][CH2:25]OS(C1C=CC(C)=CC=1)(=O)=O.C(Cl)[Cl:38]>[Zn]>[Cl:23][CH2:24][CH2:25][O:17][C:5]1[C:6]2[C:11]([C:12]([O:16][CH2:21][CH2:20][Cl:38])=[C:13]3[C:4]=1[CH:3]=[C:2]([CH3:1])[CH:15]=[CH:14]3)=[CH:10][CH:9]=[CH:8][CH:7]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 702EthanolHCID 6344DichloromethaneHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 67732-MethylanthraquinoneHCID 14798Sodium Hydroxide

Product 1

HCID 133054499,10-Bis(2-chloroethoxy)-2-methylanthracene

Reagents, catalysts & solvents

1
HCID 23994ZincCatalyst

Procedure

A 22.2 g. portion of 2-methylanthraquinone is reduced with 10 g. of zinc and 200 ml. of 20% sodium hydroxide in 40 ml. of ethanol, then alkylated with 50 ml. of 2-chloroethyl-p-toluene sulfonate as described in Example 1. The crude product is taken up in methylene chloride, filtered, dried over magnesium sulfate and concentrated to dryness. Recrystallization from 100 ml. of propanol gives 0.7 g. of the desired intermediate as a yellow solid, m.p. 82°-85° C.

Workup

  1. filtrationfiltered
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to dryness
  4. customRecrystallization from 100 ml
  5. customof propanol gives 0.7 g

Sources & evidence

ORD record
ord-a2e409b794a84f0095c4e2829b1c4c8a
Source dataset
uspto-grants-1983_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04419354

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes