2,3-Dimethylphenol → HCID 18616902, compound

HRID 1468479Notes

Reaction equation

HRID 1468479 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[O:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH2:11]1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1

Participants

5

Reactant 2

HCID 106872,3-DimethylphenolHCID 186148Pyran

Product 1

HCID 18616902HCID 18616902, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8471TriethylamineCatalyst

Procedure

In a manner similar to Preparation 27 except use 2,3-Dimethylphenol (20 g, 0.164 mol), 1,2-dihyropyran (17.9 mL, 0.196 mol), p-toluenesulfonic acid (1.64 mmol), and triethylamine (1.80 mmol) to give 33.0 g (100%) of 2-(2,3-dimethylphenoxy)tetrahydro-2H-pyran as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.02 (t, J=7.8 Hz, 1H), 6.94 (d, J=8.1 Hz, 1H), 6.79 (d, J=7.4 Hz, 1H), 5.38 (t, J=3.2 Hz, 1H), 3.95-3.81 (m, 1H), 3.58 (dtd, J=11.2, 4.1, 1.3 Hz, 1H), 2.26 (s, 3H), 2.18 (s, 3H), 2.08-1.97 (m, 1H), 1.91-1.85 (m, 2H), 1.74-1.57 (m, 3H). 13C NMR (101 MHz, CDCl3) δ 155.00, 137.89, 125.92, 125.85, 123.15, 112.16, 96.46, 62.07, 30.75, 25.48, 20.23, 19.15, 11.90.

Workup

  1. customIn a manner similar to Preparation 27

Sources & evidence

ORD record
ord-890520251ff84cdc85031fda69e183f8
Source dataset
uspto-grants-2015_04
Patent number
US09000108B2

Reaction notes

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