1,2-Dichloroethane → 2-[(6-Bromohexanoyl)oxy]propyl acrylate

HRID 424304

Reaction equation

HRID 424304 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:10]([O:14][CH2:15][CH:16](O)[CH3:17])(=[O:13])[CH:11]=[CH2:12].C(Cl)CCl>C(Cl)Cl>[C:10]([O:14][CH2:15][CH:16]([O:8][C:7](=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[CH3:17])(=[O:13])[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 202106-Bromohexanoic acidHCID 612492-Hydroxypropyl acrylate

Product 1

HCID 590050292-[(6-Bromohexanoyl)oxy]propyl acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. cooled mixture of 6-bromohexanoic acid (9.89 g), 2-hydroxypropyl acrylate (6 g), in CH2Cl2 (30 ml), EDC (7.89 g) was added. After being stirred for 30 min the reaction mixture was diluted with additional 20 ml of CH2Cl2 and stirring was continued for 16 h at room temperature. It was then filtered over celite and the filtrate was evaporated to dryness. The obtained beige-yellow residue was purified by silica column chromatography to give nearly pure material as transparent oil.

Workup

  1. stirringstirring
  2. waitwas continued for 16 h at room temperature
  3. filtrationIt was then filtered over celite
  4. customthe filtrate was evaporated to dryness
  5. customThe obtained beige-yellow residue was purified by silica column chromatography
  6. customto give nearly pure material as transparent oil

Sources & evidence

ORD record
ord-0e5407f232de4411a3a215497f6e7f7d
Source dataset
uspto-grants-2012_01
Patent number
US08105662B2

Linked notes

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