4-Methoxybenzyl alcohol → 5-Hydroxy-4-[(4-methoxyphenyl)methoxy]-2,6,6-trimethyl-2-cyclohepten-1-one

HRID 2258500Notes

Reaction equation

HRID 2258500 reaction equation
[O:1]1[CH:8]2[CH:2]1[CH:3]=[C:4]([CH3:12])[C:5](=[O:11])[CH2:6][C:7]2([CH3:10])[CH3:9].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=1>O1CCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:1][CH:8]1[C:7]([CH3:10])([CH3:9])[CH2:6][C:5](=[O:11])[C:4]([CH3:12])=[CH:3][CH:2]1[O:20][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 77384-Methoxybenzyl alcoholHCID 5577063,6,6-Trimethyl-8-oxabicyclo[5.1.0]oct-2-en-4-one

Product 1

HCID 229223315-Hydroxy-4-[(4-methoxyphenyl)methoxy]-2,6,6-trimethyl-2-cyclohepten-1-oneYield 51%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of eucarvone-4,5-oxide, i.e. 4,5-epoxy-2,6,6-trimethyl-2-cyclohepten-1-one (50 g, 0.3M), in tetrahydrofuran (150 ml), 4-methoxybenzyl alcohol (55 g, 0.4M) and p-toluenesulfonic acid (2 g) were added, and it was heated under reflux for eight hours, concentrated, and then purified by silica gel column chromatography using hexane-ethyl acetate (10:1) as an eluent to obtain 46.7 g (50%) of 5-hydroxy-4-(4-methoxybenzyloxy)-2,6,6-trimethyl-2-cyclohepten-1-one (AUM09) as a light yellow oily product.

Workup

  1. temperatureit was heated
  2. temperatureunder reflux for eight hours
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-4909384c81e6492398071a54f16d1227
Source dataset
uspto-grants-1997_08
Patent number
US05661166

Reaction notes

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