Cetyl Alcohol → HCID 67323709, compound

HRID 1810717Notes

Reaction equation

HRID 1810717 reaction equation
[OH:1][C:2]([CH:4]=[CH:5][C:6]1[CH:24]=[CH:23][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:22])[C:19]([CH3:21])=[CH2:20])=[CH:8][CH:7]=1)=[O:3].[CH2:25](O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C>[CH2:40]([O:3][C:2]([CH:4]=[CH:5][C:6]1[CH:24]=[CH:23][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:22])[C:19]([CH3:21])=[CH2:20])=[CH:8][CH:7]=1)=[O:1])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25]

Participants

5

Reactant 3

HCID 2682Cetyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 67322679HCID 67322679, compound

Product 1

HCID 67323709HCID 67323709, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a 250-mL round-bottom flask were added 2-methyl-acrylic acid 6-[4-(2-hydroxycarbonyl-vinyl)-phenoxy]-hexyl ester (4.98 g, 15.0 mmol), 1-hexadecanol (4.00 g, 16.5 mmol) and DMAP (92 mg, 0.75 mmol) as solids and a stirbar. The flask was purged with N2, followed by the addition of CH2Cl2 (35 mL). The suspension was stirred at room temperature for 20 min to give a white slurry. The flask was cooled in an ice bath and DCC (3.25 g, 15.75 mmol) was introduced. The mixture quickly became a light yellow solution, which was then removed from the ice bath and stirred at room temperature. After 20 h, the resulting white slurry was loaded on a SiO2 column (˜100 g) for quick purification. The product was eluted off with 10% EtOAc in hexanes. The fractions with the desired product were combined, concentrated and then dried in vacuo to a white solid (7.17 g, 86%) of Addition Monomer 7.

Workup

  1. customThe flask was purged with N2
  2. additionfollowed by the addition of CH2Cl2 (35 mL)
  3. customto give a white slurry
  4. temperatureThe flask was cooled in an ice bath
  5. customwas then removed from the ice bath
  6. stirringstirred at room temperature
  7. waitAfter 20 h
  8. customthe resulting white slurry was loaded on a SiO2 column (˜100 g) for quick purification
  9. washThe product was eluted off with 10% EtOAc in hexanes
  10. concentrationconcentrated
  11. dry with materialdried in vacuo to a white solid (7.17 g, 86%) of Addition Monomer 7

Sources & evidence

ORD record
ord-e05990fe33f048b99a112a41e015386c
Source dataset
uspto-grants-2013_01
Patent number
US08362151B2

Reaction notes

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