Menthofuran → 7a-Hydroxy-3,6-dimethyl-5,6,7,7a-tetrahydro-1-benzofuran-2(4H)-one

HRID 2085013Notes

Reaction equation

HRID 2085013 reaction equation
[CH3:1][CH:2]1[C:6](=[O:7])[O:5][C:4]2[CH2:8][C@H:9]([CH3:12])[CH2:10][CH2:11][C:3]1=2.CC1C2CCC(C)CC=2[O:16]C=1>>[OH:16][C:4]12[CH2:8][CH:9]([CH3:12])[CH2:10][CH2:11][C:3]1=[C:2]([CH3:1])[C:6](=[O:7])[O:5]2

Participants

3

Reactant 2

HCID 329983MenthofuranHCID 10197860HCID 10197860, compound

Product 1

HCID 1562037a-Hydroxy-3,6-dimethyl-5,6,7,7a-tetrahydro-1-benzofuran-2(4H)-one

Procedure

The chemical structure of (6R)-4,5,6,7-tetrahydro-3,6-dimethyl-3H-benzo [b]furan-2-one is known. In fact, K. Schulte-Elte et al in Tetrahedron (1967), 23(6), 2583-2599 identified the compound of the formula (I) in a mixture of lactones resulting from the photooxidation of menthofuran. Furthermore, J. Hirsch et al in J. Org. Chem. (1967), 32(9), 2915-2916 also identified the lactone (I) from among other end products resulting from the hydrolysis of α,α′-dimethoxydihydromenthofuran. However, these authors specify that the lactone (I) oxidises very easily under the synthesis conditions described to give a hydroxylactone, 5,6,7,7a-tetrahydro-7a-hydroxy-3,6-dimethyl-4H-benzo[b]furan-2-one of the formula

Workup

  1. customresulting from the hydrolysis of α,α′-dimethoxydihydromenthofuran
  2. customoxidises very easily under the synthesis conditions

Sources & evidence

ORD record
ord-56be1e1a8ef245a5b6382215c08830ca
Source dataset
uspto-grants-2004_04
Patent number
US06720302B2

Reaction notes

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