p-Ethynyltoluene → HCID 70220377, compound

HRID 565158Notes

Reaction equation

HRID 565158 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[CH:8])=[CH:3][CH:2]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1CCCC1>[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[C:8][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 13018p-EthynyltolueneHCID 21267611HCID 21267611, compound

Product 1

HCID 70220377HCID 70220377, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31268PyrrolidineSolvent

Conditions

Temperature
80 °C

Procedure

25.0 g of p-tolylacetylene and 12.71 g of tetrakis(triphenylphosphine)palladium(0) (9.2% of Pd) were introduced into 500 ml of pyrrolidine, and 65.36 g of [4-(4-bromophenyl)cyclohexyl]methanol were added quickly. The mixture was then warmed at 80° C. for 2.5 hours with stirring, cooled and subjected to conventional work-up, giving [4-(4-p-tolylethynylphenyl)cyclohexyl]methanol as a crystalline solid.

Workup

  1. additionwere added quickly
  2. temperaturecooled

Sources & evidence

ORD record
ord-5e90f8346f504e259cb7f14222bec2ac
Source dataset
uspto-grants-2001_01
Patent number
US06171664B2

Reaction notes

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