Myristyl bromide → HCID 67508433, compound

HRID 874703Notes

Reaction equation

HRID 874703 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]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[OH:24].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:2]([O:24][C:18]1[C:19]([CH3:23])=[CH:20][CH:21]=[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 8208Myristyl bromideHCID 113352,6-DimethylphenolHCID 11430Potassium Carbonate

Product 1

HCID 67508433HCID 67508433, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product was generated via general protocol A using 1-bromotetradecane (44.7 mL, 0.147 mol), 2,6-dimethylphenol (20.0 g, 0.162 mol), K2CO3 (81.3 g, 0.588 mol) and CH3CN (150 mL). Yielded 46.5 g (99.3%) of a yellow/orange liquid. 1H NMR (CDCl3, 400 MHz) δ: 7.01 (d, 4J=7.3 Hz, 2H, Ar—H), 6.91 (t, 3J=6.8 Hz, 3H, Ar—H), 3.76 (t, 3J=6.7 Hz, 2H, OCH2), 2.28 (s, 6H, Ar—CH3), 1.81 (p, 3J=7.1 Hz, 2H, OCH2CH2), 1.50 (p, 3J=7.4 Hz, 2H, OCH2CH2CH2), 1.36-1.27 (m, 22H), 0.89 (t, 3J=6.9 Hz, 3H, CH2CH3). 13C NMR (CDCl3, 100 MHz) δ: 156.08, 130.95, 128.71, 123.54, 77.32, 77.00, 76.68, 72.28, 31.93, 30.44, 29.70, 29.68, 29.66, 29.63, 29.57, 29.37, 26.16, 22.69, 16.26, 14.12.

Sources & evidence

ORD record
ord-7dbee767a78e49499a67876a8e7e6622
Source dataset
uspto-grants-2015_03
Patent number
US08980925B2

Reaction notes

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