Guaiacol → HCID 54428598, compound

HRID 1484394Notes

Reaction equation

HRID 1484394 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:11])[CH3:10])=[CH:5][CH:4]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20]>>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:10][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[OH:11]

Participants

3

Reactant 2

HCID 460GuaiacolHCID 1011481-(4-Methoxyphenyl)ethanol

Product 1

HCID 54428598HCID 54428598, compound

Procedure

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol (30 mg, 1.4×10−4 mol) and wet Raney Ni 4200 (25 mg, 4.2×10−4 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 18 hours and the reaction mixture is cooled. Nickel was removed with a magnet. Concentration gave 25 mg of a reaction mixture which is, according to analysis by HNMR, is 1-(4-methoxyphenyl)ethan-1-ol and 2-methoxyphenol. The β-O-4 bond was 100% broken.

Sources & evidence

ORD record
ord-4b01183d9fd948bba03f2e01ef2b8299
Source dataset
uspto-grants-2016_08
Patent number
US09422215B2

Reaction notes

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