Cyclohexene → HCID 18968462, compound

HRID 429900Notes

Reaction equation

HRID 429900 reaction equation
I[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC>CO.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:10]1([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH2:4][OH:5])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 8079CyclohexeneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 1076292-Iodobenzylic alcohol

Product 1

HCID 18968462HCID 18968462, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Procedure

According to example 61, 10.0 g of 2-iodobenzyl alcohol was treated with 25 mL of cyclohexene (Aldrich) using 0.96 g of Pd(OAc)2, 2.60 g of tri-ortho-tolylphosphine, and 6.6 mL of Et3N at 110° C. for 48 h. The resulting olefin mixture was hydrogenated for 6.5 h using 0.36 g of 5% Pt(C) in MeOH to afford 3.37 g (42%) of 2-cyclohexyl benzyl alcohol as a light yellow liquid.

Workup

  1. customat 110° C.
  2. customfor 48 h

Sources & evidence

ORD record
ord-2afa9822e526400e9b39808a52fe1e37
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

Loading…