HCID 70053, compound → HCID 178516049, compound

HRID 985750Notes

Reaction equation

HRID 985750 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]2[CH2:33][CH2:32][CH:31]([C:34]3[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=3)[CH2:30][CH2:29]2)=[CH:24][CH:23]=1>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[OH:21][C:22]1[CH:23]=[CH:24][C:25]([C@@H:28]2[CH2:33][CH2:32][C@H:31]([C:34]3[CH:35]=[CH:36][C:37]([OH:40])=[CH:38][CH:39]=3)[CH2:30][CH2:29]2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 70053HCID 70053, compoundHCID 11184696HCID 11184696, compound

Product 2

HCID 178516049HCID 178516049, compoundHCID 178516050HCID 178516050, compound

Procedure

More particularly, 1,4-bis(4-hydroxyphenyl)-1-cyclohexene is hydrogenated, and the resulting reaction mixture which contains 4-(4′-(4″-hydroxyphenyl)cyclohexyl)-1-hydroxybenzene is subjected to conventional purification methods to provide a purified product, and the product is then dissolved in an organic solvent which is suitably used in column separation processes, such as methanol, acetonitrile or tetrahydrofuran, or alternatively, the reaction mixture obtained is subjected to solvent replacement by an organic solvent which is suitably used in column separation processes, such as methanol, acetonitrile or tetrahydrofuran. Then, the resulting solution of the product or the solution of the reaction mixture in such an organic solvent as mentioned above is subjected to cis-trans separation operations by a suitable means such as preparative high performance liquid chromatography making use of difference of retention time so that the cis- and trans-isomer, that is, 4-(trans-4′-(4″-hydroxyphenyl)cyclohexyl)-1-hydroxybenzene and 4-(cis-4′-(4″-hydroxyphenyl)cyclohexyl) 1-hydroxybenzene, are separately obtained.

Workup

  1. customthe resulting reaction mixture which
  2. customis subjected to conventional purification methods
  3. customto provide a purified product
  4. dissolutionthe product is then dissolved in an organic solvent which
  5. customis suitably used in column separation processes, such as methanol, acetonitrile or tetrahydrofuran
  6. customalternatively, the reaction mixture obtained
  7. customis suitably used in column separation processes, such as methanol, acetonitrile or tetrahydrofuran
  8. customabove is subjected to cis-trans separation operations by a suitable means such as preparative high performance liquid chromatography

Sources & evidence

ORD record
ord-5dd69dcf06ff40a6a71231b07b4376c5
Source dataset
uspto-grants-2005_03
Patent number
US06872858B2

Reaction notes

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