1,2-Dichloroethane → (2S)-2-methylbutyl 2,5-bis[(4-{[6-(acryloyloxy)hexyl]oxy}benzoyl)oxy]benzoate

HRID 424308Notes

Reaction equation

HRID 424308 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].O[C:23]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][C:24]=1[C:25]([O:27][CH2:28][C@@H:29]([CH3:32])[CH2:30][CH3:31])=[O:26].[CH2:38](Cl)[CH2:39]Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][C:23]2[CH:36]=[CH:35][C:34]([O:37][C:17](=[O:18])[C:16]3[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][C:1](=[O:4])[CH:38]=[CH2:39])=[CH:21][CH:20]=3)=[CH:33][C:24]=2[C:25]([O:27][CH2:28][C@@H:29]([CH3:32])[CH2:30][CH3:31])=[O:26])=[O:18])=[CH:20][CH:21]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidHCID 59005024(2S)-2-methylbutyl 2,5-dihydroxybenzoate

Product 1

HCID 59005014(2S)-2-methylbutyl 2,5-bis[(4-{[6-(acryloyloxy)hexyl]oxy}benzoyl)oxy]benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture consisting of 4-{[6-(acryloyloxy)hexyl]oxy}benzoic acid (2.92 g), (2S)-2-methylbutyl 2,5-dihydroxybenzoate (1.1 g), DMAP (0.24 g) and EDC (2 g) in CH2Cl2 (30 ml) was stirred for 6 h at room temperature. The yellowish reaction mixture was then evaporated to dryness and the obtained pasty residue was purified by column chromatography over silica to give nearly pure material as transparent oil which becomes pasty upon standing for about 24 h.

Workup

  1. customThe yellowish reaction mixture
  2. customwas then evaporated to dryness
  3. customthe obtained pasty residue was purified by column chromatography over silica
  4. customto give nearly pure material as transparent oil which
  5. waitupon standing for about 24 h.

Sources & evidence

ORD record
ord-14bc3a45110c4d50afb991f214510206
Source dataset
uspto-grants-2012_01
Patent number
US08105662B2

Reaction notes

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