1-Bromohexadecane → HCID 58947033, compound

HRID 874706Notes

Reaction equation

HRID 874706 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:12]([O:14][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])[CH:13]=[C:4]([C:3]([O:2][CH3:1])=[O:15])[CH:5]=1

Participants

5

Reactant 3

HCID 82131-BromohexadecaneHCID 11430Potassium CarbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 58947033HCID 58947033, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product was generated using general protocol D using dimethyl-5-hydroxyisophthalate (3.920 g, 18.7 mmol), 1-bromohexadecane (5.18 g, 17.0 mmol), K2CO3 (9.37 g, 67.8 mmol), CH3CN (100 mL) yielded 6.30 g (86.5%) of a white solid. 1H NMR (CDCl3, 600 MHz) δ: 8.26 (t, 3J=1.4 Hz, 1H, Ar—H), 7.74 (d, 3J=1.5 Hz, 2H, Ar—H), 4.03 (t, 3J=6.5 Hz, 2H, O—CH2), 3.94 (s, 6H, COO—CH3), 1.80 (p, 3J=7.3 Hz, 2H, OCH2CH2), 1.46 (p, 3J=7.6 Hz, 2H, OCH2CH2CH2), 1.26 (m, 24H), 0.88 (t, 3J=6.8, 3H, CH2—CH3.

Sources & evidence

ORD record
ord-49312266d8964a1286455b8a0a5a9a27
Source dataset
uspto-grants-2015_03
Patent number
US08980925B2

Reaction notes

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