6-Chrysenecarbaldehyde → 12-Ethoxychrysene-6-carbaldehyde

HRID 2413595Notes

Reaction equation

HRID 2413595 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:15](=[C:16]3[C:21]=1[CH:20]=[CH:19][CH:18]=[CH:17]3)[CH:14]=[CH:13][C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=1)[CH3:2].C1C2C=CC3C(=CC([CH:40]=[O:41])=C4C=3C=CC=C4)C=2C=CC=1>C1COCC1>[CH2:1]([O:3][C:4]1[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:6](=[C:7]3[C:12](=[C:13]([CH:40]=[O:41])[CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 124387746-ChrysenecarbaldehydeHCID 144233156-Ethoxychrysene

Product 1

HCID 1337539112-Ethoxychrysene-6-carbaldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Ethoxychrysene (Cambridge Chemical, Inc., 48 g, 0.176 mol) was formylated according to the procedure outlined in 1A, except that CH2Cl2 (1L) was used as the reaction solvent. After isolation, the crude material was chromatographed on a plug of SiO2 (500 g) using CH2Cl2 as the eluting solvent to give (after removal of solvent and drying) 33.7 g (64%) of 12-ethoxychrysene-6-carbaldehyde mp 173.5°-176°, (C,H).

Workup

  1. customAfter isolation, the crude material was chromatographed on a plug of SiO2 (500 g)

Sources & evidence

ORD record
ord-e0c2b287004644ffafc46b43ccde53e0
Source dataset
uspto-grants-1988_01
Patent number
US04719048

Reaction notes

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