HCID 18436351, compound → HCID 18436342, compound

HRID 351443Notes

Reaction equation

[CH2:1]([CH:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:6][CH:5]([CH2:24][OH:25])[CH:4]1[CH3:26])[CH3:2].[CH2:27]([CH:29]1[CH:34]([C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=2)[C:33]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=2)=[CH:32][CH:31]([CH2:50][OH:51])[CH:30]1[CH3:52])[CH3:28]>C(Cl)Cl.C(OCC)(=O)C.O.Cl[Ti](Cl)(Cl)Cl>[CH2:1]([CH:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[C:7]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[CH2:6][CH:5]([CH2:24][OH:25])[CH:4]1[CH3:26])[CH3:2].[CH2:27]([CH:29]1[CH:30]([CH3:52])[CH:31]([CH2:50][OH:51])[CH2:32][CH:33]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=2)[CH:34]1[C:35]1[CH:36]=[CH:37][C:38]([OH:41])=[CH:39][CH:40]=1)[CH3:28]

Participants

Conditions

Temperature: -10 °C

Procedure

To the above mixture of 4-[6-ethyl-4-hydroxymethyl-2-(4-methoxy-phenyl)-5-methyl-cyclohex-1-enyl]-phenol and 4-[6-ethyl-4-hydroxymethyl-2-(4-methoxy-phenyl)-5-methyl-cyclohex-2-enyl]-phenol (380 mg) in DCM (10 mL) at −10° C. was added TiCl4 (0.180 mL) and the mixture was stirred for 3 h at −10° C. The reaction mixture was diluted with ethyl acetate/H2O (200/100 mL). The organic layer was dried and purified on SiO2 to yield two products 4-[6-ethyl-4-hydroxymethyl-2-(4-methoxy-phenyl)-5-methyl-cyclohex-1-enyl]-phenol and 4-[2-ethyl-4-hydroxymethyl-6-(4-methoxy-phenyl)-3-methyl-cyclohexyl]-phenol.

Workup

customThe organic layer was dried
custompurified on SiO2

Sources & evidence

ORD record: ord-11c931c4f05d455080e736269a745303
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183445B2

Reaction notes

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