4-Methylcyclohexane-1,2-diol → 4-Methylcatechol
Reaction equation
[OH:1][CH:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][CH2:4][C:3]1=[O:9].OC1CCC(C)CC1=O.CC1CCC(O)C(O)C1>>[CH3:8][C:6]1[CH:7]=[C:2]([OH:1])[C:3](=[CH:4][CH:5]=1)[OH:9]Participants
4
Procedure
4-Methyl catechol (25 mg, 2×10−4 mol) and wet Raney Ni 4200 (12 mg, 2×10−4 mol, 100 mol %) is weighed into a reaction flask under argon. Degassed i-PrOH (5 mL) is added and the flask is capped with a rubber septa and the mixture is heated (80° C.). The reaction is run for 24 hours and the reaction mixture is cooled. Nickel was removed with a magnet. Concentration gave 20 mg of a reaction mixture which is, according to analysis by HNMR, a complex mixture of mainly, 2-hydroxy-4-methyl-Cyclohexanone; 2-hydroxy-5-methyl-Cyclohexanone; 4-methyl-1,2-Cyclohexanediol. The aromatic ring was saturated.
Sources & evidence
- ORD record
- ord-e2bcc818c5c0429f8459defc7ad54d8c
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422215B2
Reaction notes
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