8-(3,4-Dichlorophenyl)oct-7-yn-1-ol → HCID 18470154, compound

HRID 2228894Notes

Reaction equation

HRID 2228894 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH:5]=[CH:6][C:7]=1[Cl:8]>CO.[Pt](=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 184701968-(3,4-Dichlorophenyl)oct-7-yn-1-ol

Product 1

HCID 18470154HCID 18470154, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-(3,4-dichlorophenyl)-oct-7-yn-1-ol (0.70 g) in methanol (20 ml) was added platinum dioxide (0.05 g) and the mixture reacted under an atmosphere of hydrogen (initial pressure 50 psi). After 1 h. the catalyst was filtered through Hyflo and washed with methanol. The combined methanol layers were evaporated under reduced pressure to give 8-(3,4-dichlorophenyl)octan-1-ol (0.69 g). 1H-NMR (CDCl3) δ 1.1-1.8 (12H, m), 2.55 (2H, t), 3.64 (2H, m), 6.99 (1H, dd) and 7.2-7.4 (2H, m).

Workup

  1. customthe mixture reacted under an atmosphere of hydrogen (initial pressure 50 psi)
  2. filtrationAfter 1 h. the catalyst was filtered through Hyflo
  3. washwashed with methanol
  4. customThe combined methanol layers were evaporated under reduced pressure

Sources & evidence

ORD record
ord-47df156786ad42bcbed48f9937a57656
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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