Acetic Anhydride → HCID 23356093, compound

HRID 233627Notes

Reaction equation

HRID 233627 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6](O)[C:5]2[C:10]([C:12]3[C:17]([C:18](=[O:19])[C:4]=2[C:3]=1O)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:11].[C:21](OC(=O)C)(=[O:23])[CH3:22].CN(C1C=CC=CN=1)C.[C:37](OCC)(=[O:39])[CH3:38]>C(Cl)Cl>[C:21]([C:6]1[C:5]2[C:10](=[O:11])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18](=[O:19])[C:4]=2[C:3]([C:37](=[O:39])[CH3:38])=[C:2]([CH3:1])[C:7]=1[CH3:8])(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 218852-DimethylaminopyridineHCID 1005741,4-Dihydroxy-2,3-dimethyl-9,10-anthraquinone

Product 1

HCID 23356093HCID 23356093, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2,3-dimethylquinizarin (5.00 g, 18.637 mmol) in dry CH2Cl2 (250 ml) was added acetic anhydride (40 ml) pyridine (40 ml) and dimethylaminopyridine (DMAP, 1.7 g) at room temperature under argon. After two hours, the reaction mixture was poured into a mixture of ethyl acetate and ice (1:1, 800 ml), extracted with CH2Cl2, and the combined organic layers were dryed over MgSO4. Flash chromatography with toluene and ethylacetate; (95.5%) gave 2.517 g of pure compound (38% yield). (MP: 222°-224° C.). 1H NMR (CDCl3) δ:2.27 (s, 6H, CH3, 2.53 (s, 6H, COCH3), 7.72 (m, 2H, ArH), 8.15 (m, 2H, ArH).

Workup

  1. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-fa0b748bb55549fd8c951abda2e5d3b4
Source dataset
uspto-grants-1997_01
Patent number
US05593970

Reaction notes

Loading…