6-Chrysenecarbaldehyde → 12-Ethoxychrysene-6-carbaldehyde

HRID 1193734Notes

Reaction equation

HRID 1193734 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>C(Cl)Cl>[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 6344DichloromethaneSolvent

Procedure

6-Ethoxychrysene (Cambridge Chemical, Inc., 48 g, 0.176 mol) was formylated according to the procedure outlined in 1A, except that CH2Cl2 (1 L) 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-e6096158fd93495dbc6dc5a93b1ef732
Source dataset
uspto-grants-1989_03
Patent number
US04810727

Reaction notes

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