Dichloromethane → 12-Chloro-6-chrysenecarbaldehyde

HRID 1761998Notes

Reaction equation

HRID 1761998 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH:12]=[CH:11][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=1.C1C2C=CC3C(=CC([CH:38]=[O:39])=C4C=3C=CC=C4)C=2C=CC=1.C(Cl)Cl>CCOC(C)=O>[Cl:1][C:2]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:4](=[C:5]3[C:10](=[C:11]([CH:38]=[O:39])[CH:12]=2)[CH:9]=[CH:8][CH:7]=[CH:6]3)[CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 56969Chrysene, 6-chloro-HCID 124387746-Chrysenecarbaldehyde

Product 1

HCID 1337538912-Chloro-6-chrysenecarbaldehyde

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6-Chlorochrysene (Cambridge Chemical, Inc., 70 g, 0.266 mol) was formylated according to the procedure outlined in 1A, except that CH2Cl2 (2.5 L) was used as the reaction solvent. Chromatography on a plug of SiO2 (1 kg) using EtOAc as the eluting solvent afforded after removal of solvent and drying 19.1 g (25%) of 12-chloro-6-chrysenecarbaldehyde mp 255°-257°, (EtOAc).

Workup

  1. customafforded
  2. customafter removal of solvent
  3. dry with materialdrying 19.1 g (25%) of 12-chloro-6-chrysenecarbaldehyde mp 255°-257°, (EtOAc)

Sources & evidence

ORD record
ord-ea1e8fd03a024186b715b63eab9e2c41
Source dataset
uspto-grants-1989_05
Patent number
US04829090

Reaction notes

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