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

HRID 2413662Notes

Reaction equation

HRID 2413662 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-f35f284c4fc0496eb2a0443ab299a98a
Source dataset
uspto-grants-1988_01
Patent number
US04719049

Reaction notes

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