2-Methylresorcinol → 3-(Cyclohexylmethoxy)-2-methylphenol

HRID 74419

Reaction equation

[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].Br[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH:12]1([CH2:11][O:8][C:7]2[C:2]([CH3:1])=[C:3]([OH:9])[CH:4]=[CH:5][CH:6]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Reactant 2

HCID 118432-Methylresorcinol

HCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 431432823-(Cyclohexylmethoxy)-2-methylphenol

Procedure

Alkylation of 2-methylbenzene-1,3-diol using (bromomethyl)cyclohexane following the method used in Example 154 gave 3-(cyclohexylmethoxy)-2-methylphenol. Yield (0.58 g, 37%): 1H NMR (400 MHz, CDCl3) δ 6.98 (t, J=8.0 Hz, 1H), 6.42 (t, J=7.6 Hz, 2H), 4.60 (bs, 1H), 3.72 (d, J=6.4 Hz, 2H), 2.12 (s, 3H), 1.68-1.89 (m, 6H), 1.16-1.35 (m, 3H), 1.01-1.11 (m, 2H).

Sources & evidence

ORD record: ord-91ea1935be7d4b88b8f46a9d71815531
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829244B2

Linked notes

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