Methanol → HCID 178498355, compound

HRID 371297Notes

Reaction equation

HRID 371297 reaction equation
[OH:1][C:2]1[C:23]2[C:22](=[O:24])[C:9]3[O:10][C:11](=[O:21])[C:12]4[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([O:19][CH3:20])[C:13]=4[C:8]=3[C:7](=[O:25])[C:6]=2[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:29])(=O)=O.[CH3:31][OH:32]>C(O)(=O)C.C(Cl)Cl>[OH:32][C:31]1[C:22](=[O:24])[C:23]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[OH:1])[C:7](=[O:25])[C:8]=1[C:13]1[C:14]([O:19][CH3:20])=[CH:15][C:16]([CH3:18])=[C:17]([Cl:29])[C:12]=1[C:11]([O:10][CH3:9])=[O:21]

Participants

6

Reactant 3

HCID 887MethanolHCID 24648Sulfuryl chlorideHCID 156387WS-5995 A

Product 1

HCID 178498355HCID 178498355, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

8-Hydroxy-1-methoxy-3-methyl-7,12-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-5,7,12-trione (400 mg) as prepared in Example 1 was dissolved in a 20:100:1 mixture (20 ml) of acetic acid, methylene chloride and methanol, followed by addition of sulfuryl chloride (2 ml). The mixture was refluxed for 5 hours. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography to give methyl 2-(3,5-dihydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methyl-6-chlorobenzoate.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e7c7f8f9b0534bc4ad5c4a03ec020a71
Source dataset
uspto-grants-1985_07
Patent number
US04530845

Reaction notes

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