4-Methoxyphenol → 12-[(2-Methylacryloyl)amino]dodecanoic acid

HRID 978174Notes

Reaction equation

HRID 978174 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].[OH-].[Na+].COC1C=CC(O)=CC=1>O1CCOCC1.O>[C:1]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

7

Reactant 4

HCID 90154-MethoxyphenolHCID 13528Methacryloyl chlorideHCID 14798Sodium HydroxideHCID 6966112-Aminododecanoic Acid

Product 1

HCID 1938658512-[(2-Methylacryloyl)amino]dodecanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The same procedure as described above is utilized with 5.4 g (0.052 mol) of methacryloyl chloride, 10 g (0.047 mol) of 12-aminododecanoic acid, 4.4 g (0.01 mol) of sodium hydroxide, and p-methoxyphenol in a mixed solvent (H2O:Dioxane=50:50) at 0°-5° C. Yield after recrystallized from ethyl acetate is 10 g (75%). Melting point 70.8°-72.4° C. NMR (DMSO-d6), 7.8 gamma (br s, 1H, NH), 5.5 gamma (br s, 1H, =CH2), 5.2 gamma (br s, 1H, =CH2), 3.0 gamma (t, 2H, NCH2), 2.1 gamma (t, 2H, CH2COOH), 1.7 gamma (s, 3H, CH3), 1.2 gamma (br s, 18H, (CH2)9).

Workup

  1. customYield
  2. customafter recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5574e915f19f430dbb848b869c0993c3
Source dataset
uspto-grants-1987_05
Patent number
US04663409

Reaction notes

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