10-Chloro-1-anthracenemethanol → 10-Chloroanthracene-1-carbaldehyde

HRID 1381798Notes

Reaction equation

HRID 1381798 reaction equation
[Cl:1][C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[CH2:16][OH:17]>C(Cl)Cl>[Cl:1][C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[CH:16]=[O:17]

Participants

3

Reactant 1

HCID 1337541110-Chloro-1-anthracenemethanol

Product 1

HCID 1439124510-Chloroanthracene-1-carbaldehydeYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10-Chloro-1-anthracenemethanol (37C, 8.8 g, 0.036 mol) was dissolved in CH2Cl2 (200 ml) and treated with BaMnO4 (Aldrich, 15 g, 0.059 mol) for 3 days and briefly brought to reflux. The reaction mixture was filtered, and the filtrate reduced to dryness. The residue was chromatographed by preparative HPLC using PhCH3 as the eluting solvent to give 6.0 g (69%) of crude 10-chloroanthracene-1-carboxaldehyde, which was used without further purification. An analytical sample was recrystallized from CH2Cl2 /hexane mp 139°-140.5° . (C, H, Cl).

Workup

  1. temperatureto reflux
  2. filtrationThe reaction mixture was filtered
  3. customThe residue was chromatographed by preparative HPLC

Sources & evidence

ORD record
ord-7b9a15c9ac6d480cbb0d5d8e087c4e5f
Source dataset
uspto-grants-1989_02
Patent number
US04803221

Reaction notes

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