Myristyl bromide → HCID 67507655, compound

HRID 874701Notes

Reaction equation

HRID 874701 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[C:22]([CH3:23])=[CH:21][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][CH:21]=[C:22]([CH3:23])[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 106872,3-DimethylphenolHCID 11430Potassium Carbonate

Product 1

HCID 67507655HCID 67507655, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product was generated via general protocol A using 1-bromotetradecane (45.0 mL, 147.9 mmol), 2,3-dimethylphenol (20.15 g, 163.3 mmol), K2CO3 (81.76 g, 591.6 mmol) and CH3CN (200 mL). Yielded 36.6 g (77.7%) of a brown liquid. 1H NMR (CDCl3, 400 MHz) δ: 7.03 (t, 3J=7.8 Hz, 1H, Ar—H), 6.76 (d, 3J=7.4 Hz, 1H, Ar—H), 6.70 (d, 3J=8.1 Hz, 1H, Ar—H), 3.93 (t, 3J=6.5, 2H, O—CH2), 2.27 (s, 3H, Ar—CH3), 2.16 (s, 3H, Ar—CH3), 1.79 (p, 3J=6.9, 2H, O—CH2—CH2), 1.48 (p, 3J=7.1, 2H, O—CH2—CH2—CH2), 1.27 (m, 22H), 0.88 (t, 3J=6.3, 3H, CH2—CH3). 13C NMR (CDCl3, 100 MHz) δ: 157.20, 137.86, 125.84, 125.33, 122.08, 108.98, 68.23, 32.07, 29.86, 29.83, 29.78, 29.61, 29.58, 29.54, 26.33, 22.88, 20.17, 14.24, 11.70.

Sources & evidence

ORD record
ord-a8b1f503c592440c89e73eaaa87949f1
Source dataset
uspto-grants-2015_03
Patent number
US08980925B2

Reaction notes

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