2-Methoxy-1,3-butadiene → HCID 14575139, compound

HRID 620902

Reaction equation

HRID 620902 reaction equation
[Cl:1][C:2]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:9]([OH:17])=[C:8]2[C:3]=1[C:4](=[O:19])[CH:5]=[CH:6][C:7]2=[O:18].C[O:21][C:22]([CH:24]=[CH2:25])=[CH2:23]>C1C=CC=CC=1>[Cl:1][C:2]1[C:15]2[C:10]([C:9]([OH:17])=[C:8]3[C:3]=1[C:4](=[O:19])[CH:5]1[CH:6]([CH2:25][CH2:24][C:22](=[O:21])[CH2:23]1)[C:7]3=[O:18])=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 2

HCID 993382-Methoxy-1,3-butadieneHCID 1366779410-Chloro-8,9-dihydroxy-1,4-anthracenedione2×

Product 1

HCID 14575139HCID 14575139, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10-Chloro-8,9-dihydroxy-1,4-anthracenedione (compound 3) (100 mg), 2-methoxy-1,3-butadiene (564 mg) and dry benzene (10 ml) were heated in a sealed tube for 4 h at 130°. After cooling the crude solution was preparatively chromatographed on silica gel layers containing oxalic acid (2%) with chloroform as eluant. The major yellow band was recovered to give the product (compound 9) as a yellow crystalline solid (85 mg, 68%).

Workup

  1. customwas preparatively chromatographed on silica gel layers
  2. additioncontaining oxalic acid (2%) with chloroform as eluant
  3. customThe major yellow band was recovered

Sources & evidence

ORD record
ord-930522cb6a72465d92e7a1370956e377
Source dataset
uspto-grants-1989_04
Patent number
US04822873

Linked notes

Loading…