1-Hydroxymethyl-2,3,3-trimethyl-cyclohexa-1,5-diene → 1-Hydroxymethyl-2,3,3-trimethyl-cyclohex-6-ene

HRID 25890Notes

Reaction equation

HRID 25890 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH2:6][C:5]([CH3:10])([CH3:9])[C:4]=1[CH3:11]>C(O)C.[Ni]>[OH:1][CH2:2][C:3]1[CH:4]([CH3:11])[C:5]([CH3:10])([CH3:9])[CH2:6][CH2:7][CH:8]=1

Participants

4

Reactant 1

HCID 205694331-Hydroxymethyl-2,3,3-trimethyl-cyclohexa-1,5-diene

Product 1

HCID 213256291-Hydroxymethyl-2,3,3-trimethyl-cyclohex-6-eneYield 91.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

30.4 g of 1-hydroxymethyl-2,3,3-trimethyl-cyclohexa-1,5-diene were hydrogenated at 10°-12° in the presence of 1g of Raney-nickel in 300 ml of ethanol. 3.95 l of hydrogen were then absorbed within 2.5 h. A filtration followed by evaporation and distillation gave 28.2 g of 1-hydroxymethyl-2,3,3-trimethyl-cyclohex-6-ene. nD = 1.4862, d20 = 9.9447

Workup

  1. custom3.95 l of hydrogen were then absorbed within 2.5 h
  2. filtrationA filtration
  3. customfollowed by evaporation and distillation

Sources & evidence

ORD record
ord-91f4dcac6ae64b8d866b0c8e8c0a5112
Source dataset
uspto-grants-1979_04
Patent number
US04147672

Reaction notes

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