Hydrogen Peroxide → 2-Methyl-1-naphthol

HRID 1379307Notes

Reaction equation

HRID 1379307 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH3:12].CC1C=CC2C(=CC=CC=2)C=1B(O)[OH:25].B(O)O.OO>>[CH3:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[OH:25]

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 61668Boronic AcidHCID 757541-Bromo-2-methylnaphthaleneHCID 11401196(2-methylnaphthalen-1-yl)boronic Acid

Product 1

HCID 240552-Methyl-1-naphtholYield 51%

Procedure

Yarboro, T. L.; Karr, C.; J. Org. Chem. 1959, 24, 1141 disclose a process wherein 1-bromo-2-methyl naphthalene is convened into 2-methyl-1-naphthalene boronic acid via Grignard reaction. The boronic acid is oxidized by 30% hydrogen peroxide to produce 2-methyl-1-naphthol in 51% yield. This prior art process is disadvantageous in that it involves 4 steps and is not economical.

Sources & evidence

ORD record
ord-bc2e5f0c465649e78684c16d15779377
Source dataset
uspto-grants-1997_09
Patent number
US05670698

Reaction notes

Loading…