Phenol → HCID 19600701, compound

HRID 346008Notes

Reaction equation

HRID 346008 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-].[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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 996PhenolHCID 144227783-Diazo-2,3-dihydro-6-(phenylmethoxy)-4H-1-benzopyran-4-one

Product 1

HCID 19600701HCID 19600701, compoundYield 12.4%

Reagents, catalysts & solvents 3

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

Procedure

A solution of 17 g of 3-diazo-6-benzyloxy-4-chromanone and 17 g of phenol in 100 ml of toluene was heated to 110° C. in an oil bath. Rhodium (II) acetate dimer (50 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 2.6 g of product, m p. 100°-102° C. 1H-NMR(CDCl3)delta(ppm): 4.4 (m, 2H), 4.84 (m, 1H), 4.88 (s, 2H), 6.82-7.40 (m, 13H).

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-cfda047cc3144966b2b7893b49613ea5
Source dataset
uspto-grants-1991_10
Patent number
US05059609

Reaction notes

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