Acetic Acid → 9-Benzyl-anthracene

HRID 728520Notes

Reaction equation

HRID 728520 reaction equation
[CH:1]1[C:14]2[C:13](=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C=O.[ClH:26].[C:27](O)(=O)[CH3:28]>>[CH2:16]([C:13]1[C:14]2[C:5]([CH:6]=[C:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)=[CH:4][CH:3]=[CH:2][CH:1]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:16]([C:13]1[C:14]2[C:5]([C:27]([CH2:28][Cl:26])=[C:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)=[CH:4][CH:3]=[CH:2][CH:1]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7018AnthroneHCID 7498Benzyl Bromide

Product 2

HCID 2644019-Benzyl-anthraceneHCID 13741965HCID 13741965, compound

Procedure

According to a method reported by Sieglitz and Marx, Berichte 56, 1619(1923) and by F. H. C. Stuart, Australian J. Chem., 478(1960), 8.2 g of 9-benzyl-anthracene was synthesized from 18.9 g of anthrone and 50 g of benzyl bromide. A solution of 4.8 g of 9-benzyl bromide in 40 ml of acetic acid was chloromethylated with 3.2 g of paraformaldehyde and hydrochloride gas to give 3.4 g of 9-benzyl-10-chloromethylanthracene (mp: 146° to 147° C.) after recrystallization from benzene.

Sources & evidence

ORD record
ord-6e541d75f0c341a8a3ee12cbe033cab3
Source dataset
uspto-grants-1991_09
Patent number
US05049455

Reaction notes

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