4-Methoxyphenol → HCID 19600789, compound

HRID 487904Notes

Reaction equation

HRID 487904 reaction equation
[N+](=[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)[O:5][CH2:4]1)=[N-].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:15]([O:14][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[O:5][CH2:4][CH:3]([O:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1)[C:12]2=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 2

HCID 90154-MethoxyphenolHCID 144227783-Diazo-2,3-dihydro-6-(phenylmethoxy)-4H-1-benzopyran-4-one

Product 1

HCID 19600789HCID 19600789, compoundYield 5.4%

Reagents, catalysts & solvents 3

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 76 g of 3-diazo-6-benzyloxy-4-chromanone and 76 g of p-methoxyphenol in 450 ml of toluene was heated to 110° C. in an oil bath. Rhodium (II) acetate dimer (225 mg) was added in one portion. After nitrogen evolution ceased (5 minutes), the reaction was allowed to cool to room temperature, diluted with ethyl acetate and washed with 10% sodium hydroxide to remove excess phenol. The organic layer was dried over sodium sulfate and evaporated in vacuo to give the crude product, which was purified by column chromatography on silica gel eluting with dichloromethane to give 5.5 g of present title product; mp 98°-100° C.; 1H-NMR (CDCl3) delta (ppm) 3.85(s, 3H), 4.45-4.65 (m, 2H), 5.0-5.2 (m, 3H), 6.5-7.6 (m, 12H)

Workup

  1. custom(5 minutes)
  2. washwashed with 10% sodium hydroxide
  3. customto remove excess phenol
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated in vacuo
  6. customto give the crude product, which
  7. customwas purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-7dd8f656ca7a43359f5a2bb3842124fe
Source dataset
uspto-grants-1994_03
Patent number
US05298512

Reaction notes

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