2-(4-Hydroxy-2,6-dimethylphenyl)-3-methoxy-5-(tetrahydropyran-4-ylmethyl)cyclopent-2-enone → 2-(4-Hydroxy-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione

HRID 1193040Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:23])[CH:11]([CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:12][C:13]=2[O:14]C)=[C:4]([CH3:24])[CH:3]=1>Cl.CC(C)=O>[OH:1][C:2]1[CH:3]=[C:4]([CH3:24])[C:5]([CH:9]2[C:10](=[O:23])[CH:11]([CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:12][C:13]2=[O:14])=[C:6]([CH3:8])[CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 2-(4-hydroxy-2,6-dimethylphenyl)-3-methoxy-5-(tetrahydropyran-4-ylmethyl)cyclopent-2-enone (0.375 g, 0.0014 mol) in a mixture of 2M hydrochloric acid (3 ml) and acetone (5 ml) is heated at 120° C. for 30 minutes under microwave irradiation. The reaction mixture is concentrated in vacuo then azeotroped with toluene to afford 2-(4-hydroxy-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione as a cream solid.

Workup

concentrationThe reaction mixture is concentrated in vacuo
customthen azeotroped with toluene

Sources & evidence

ORD record: ord-4ebf8372c1ae4cfd99ad90dbf0d03591
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680339B2

Reaction notes

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