2,4-Dimethylphenol → HCID 67508466, compound

HRID 874702Notes

Reaction equation

HRID 874702 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[OH:24].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:2]([O:24][C:18]1[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=1[CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 77712,4-DimethylphenolHCID 8208Myristyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 67508466HCID 67508466, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product was generated via general protocol A using 1-bromotetradecane (44 mL, 0.149 mol), 2,4-dimethylphenol (19.5 mL, 0.164 mol), K2CO3 (82.4 g, 0.596 mol) and CH3CN (200 mL). Yielded 43.13 g (90.8%). 1H NMR (CDCl3, 600 MHz) δ: 7.00 (s, 1H, Ar—H), 6.94 (d, 3J=8.41 Hz, 1H, Ar—H), 6.75 (d, 3J=8.15 Hz, 1H, Ar—H), 3.97 (t, 3J=6.46 Hz, 2H, OCH2), 2.31 (s, 3H, Ar—CH3), 2.26 (s, 3H, Ar—CH3), 1.83 (p, 3J=7.3 Hz, 2H, O—CH2—CH2), 1.52 (p, 3J=7.6 Hz, 2H, O—CH2—CH2—CH2), 1.44-1.28 (m, 22H), 0.95 (t, 3J=7.05, 3H, CH2—CH3). 13C NMR (150 MHz) δ: 155.24, 131.45, 129.20, 126.88, 126.66, 111.08, 68.17, 53.41, 32.02, 31.90, 29.97, 29.79, 29.78, 29.76, 29.52, 29.50, 29.46, 26.24, 22.78, 20.47, 16.19, 14.19.

Workup

  1. customYielded 43.13 g (90.8%)

Sources & evidence

ORD record
ord-63606f2afabd49caa72156214b5bd261
Source dataset
uspto-grants-2015_03
Patent number
US08980925B2

Reaction notes

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