Ethanol → 1-Hexanol

HRID 1578665Notes

Reaction equation

HRID 1578665 reaction equation
[Rh:1](Cl)(Cl)[Cl:2].[C:5]1([P:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:24]1[CH:29]=[CH:28][C:27]([P:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:26][CH:25]=1.[CH:43]1[CH:48]=[CH:47][C:46]([P:49]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[CH:45][CH:44]=1.[CH:62]1[CH:67]=[CH:66][C:65](P([C:75]2[CH:80]=[CH:79]C=CC=2)C2C=CC=CC=2)=[CH:64][CH:63]=1.[Cl-].[Rh].[CH3:83]CCC=C.[CH2:88]([OH:90])[CH3:89]>C1C=CC=CC=1>[CH:21]1[CH:20]=[CH:19][C:18]([P:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH:23][CH:22]=1.[CH:40]1[CH:39]=[CH:38][C:37]([P:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]2[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=2)=[CH:42][CH:41]=1.[CH:59]1[CH:58]=[CH:57][C:56]([P:49]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:46]2[CH:47]=[CH:48][CH:43]=[CH:44][CH:45]=2)=[CH:61][CH:60]=1.[Cl-:2].[Rh:1].[CH2:88]([OH:90])[CH2:89][CH2:83][CH:80]([CH3:79])[CH3:75].[CH2:62]([OH:90])[CH2:63][CH2:64][CH2:65][CH2:66][CH3:67]

Participants

9

Reactant 5

HCID 702EthanolHCID 80041-PenteneHCID 11776TriphenylphosphineHCID 24872Rhodium chlorideHCID 84599Chlorotris(triphenylphosphine)rhodium(I)

Product 3

HCID 81031-HexanolHCID 122964-Methyl-1-pentanolHCID 84599Chlorotris(triphenylphosphine)rhodium(I)

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Chlorotris(triphenylphosphine)rhodium(I), [(03P)3RhCl], was prepared by refluxing an ethanol solution of rhodium(III) chloride in the presence of an excess amount of triphenylphosphine. Chlorotris(triphenylphosphine)rhodium(I) was dissolved in benzene, and the microspheres of Example III were added to the resulting red solution in an autoclave, equipped with a magnetic driven stirrer. Pentene-1 was introduced to the reactor along with benzene. The reaction was performed under conditions similar to Example IV. About 82% of the feed was reacted to give predominantly isohexanol and n-hexanol. The solid catalyst left inside of the reactor from this run was rinsed with fresh portions of benzene, and saved for another run.

Workup

  1. additionthe microspheres of Example III were added to the resulting red solution in an autoclave
  2. customequipped with a magnetic driven stirrer
  3. customAbout 82% of the feed was reacted

Sources & evidence

ORD record
ord-a139d5fb50024904a4df2e9a278658fa
Source dataset
uspto-grants-1976_02
Patent number
US03937742

Reaction notes

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