2-Methoxyethanol → 10-(2-Methoxyethoxy)9-anthracenecarbaldehyde

HRID 1381784Notes

Reaction equation

HRID 1381784 reaction equation
CC([O-])(C)C.[K+].Cl[C:8]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:22]=[O:23])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[CH:13]2.[CH3:24][O:25][CH2:26][CH2:27][OH:28]>O>[CH3:24][O:25][CH2:26][CH2:27][O:28][C:8]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:22]=[O:23])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[CH:13]2

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 8270310-Chloro-9-anthraldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 1337540710-(2-Methoxyethoxy)9-anthracenecarbaldehydeYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of KOtBu (MCB, 18.2 g, 0.162 mol)) in 2-methoxyethanol (1 L) was treated with 10-chloro-9-anthraldehyde (Aldrich, 25 g, 0.104 mol) and refluxed for 2 h. The cooled reaction mixture was diluted with H2O (5 L), and the resulting oil stirred for 2 h until solidification occurred. The filtered solid was chromatographed on a plug of SiO2 (500 g) using CH2Cl2 as the eluting solvent to afford 26.9 g (92%) of 10-(2-methoxyethoxy)-9-anthracenecarboxaldehyde mp 87°-88°, (C, H), (CH2Cl2 /hexane).

Workup

  1. temperaturerefluxed for 2 h
  2. customThe cooled reaction mixture
  3. customThe filtered solid was chromatographed on a plug of SiO2 (500 g)

Sources & evidence

ORD record
ord-33b6b7ed03aa473fa56178d14c991e70
Source dataset
uspto-grants-1989_02
Patent number
US04803221

Reaction notes

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