Cyclohexene → 7-hydroxy-3-(4-methoxyphenyl)-2H-1-benzopyran

HRID 254890Notes

Reaction equation

HRID 254890 reaction equation
C1CCCCC=1.C([O:14][C:15]1[CH:32]=[CH:31][C:18]2[CH:19]=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[CH2:21][O:22][C:17]=2[CH:16]=1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[OH:14][C:15]1[CH:32]=[CH:31][C:18]2[CH:19]=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[CH2:21][O:22][C:17]=2[CH:16]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 595921047-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran

Product 1

HCID 98598477-hydroxy-3-(4-methoxyphenyl)-2H-1-benzopyranYield 94.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Cyclohexene (1.5 mL) and Pd(OH)2/C (0.15 g) were added to a solution of compound 1 (0.3 g, 0.87 mmol) in ethanol (20 mL). The resultant mixture was stirred under a reflux temperature of 78° C. for 2 hrs, and then cooled to room temperature. After filtration, the filtrate was concentrated in vacuo, followed by purification via silica gel column chromatography (ethyl acetate/n-hexane=1:4), thus giving the title compound 3a as a colorless crystal (0.21 g, 94% yield).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customfollowed by purification via silica gel column chromatography (ethyl acetate/n-hexane=1:4)

Sources & evidence

ORD record
ord-e419364d7b0c47459d06fad7341fe4f6
Source dataset
uspto-grants-2011_01
Patent number
US07875735B2

Reaction notes

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