Cyclohexene → HCID 18968462, compound

HRID 369793Notes

Reaction equation

HRID 369793 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.CCN(CC)CC>CO>[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

5

Reactant 3

HCID 8079CyclohexeneHCID 8471TriethylamineHCID 1076292-Iodobenzylic alcohol

Product 1

HCID 18968462HCID 18968462, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 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(O Ac)2, 2.60 g of tri-ortho-tolyphosphine, and 6.6 mL of Et3N at 100° 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 100° C.
  2. customfor 48 h

Sources & evidence

ORD record
ord-96b7f96d77544fe2a7c284f7c33a8ecf
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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