Cyclohexene → HCID 59386503, compound

HRID 1895819Notes

Reaction equation

HRID 1895819 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([O:23]C3CCCCO3)=[CH:19][CH:18]=2)=[CH:11][CH:10]=1.C1CCCCC=1>[OH-].[Pd+2].[OH-].C(O)C>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 59386493HCID 59386493, compound

Product 1

HCID 59386503HCID 59386503, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.3 g of (E)-4-(6-hydroxyhexyloxy)-4′-(tetrahydropyran-2-yloxy)stilbene (C), 0.6 g of palladium hydroxide, 34 ml of cyclohexene and 50 ml of ethanol was refluxed for 16 hours. The cooled mixture was filtered over celite and evaporated. 2.2 g of 4-{2-[4-(6-Hydroxy-hexyloxy)-phenyl]-ethyl}-phenol (L, 86%) was obtained after dissolution in 600 ml of dichloromethane, two extractions with 50 ml of water, drying over magnesium sulphate and evaporation. Apparently, deprotection of (K) had occurred under the reaction conditions.

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationThe cooled mixture was filtered over celite
  3. customevaporated

Sources & evidence

ORD record
ord-a48422fef0634e2594123dce4fa9a4d3
Source dataset
uspto-grants-2013_08
Patent number
US08518299B2

Reaction notes

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