Acetone → 2,5-Di-[4-(6-acryloyloxyhexyloxy)benzoyloxy]benzoic acid

HRID 353002Notes

Reaction equation

HRID 353002 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:21][C:22]2[CH:29]=[CH:28][C:27]([O:30][C:31]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][O:46][C:47](=[O:50])[CH:48]=[CH2:49])=[CH:35][CH:34]=3)=[O:32])=[CH:26][C:23]=2[CH:24]=[O:25])=[O:20])=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].CC(C)=[O:53]>>[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:19]([O:21][C:22]2[CH:29]=[CH:28][C:27]([O:30][C:31]([C:33]3[CH:34]=[CH:35][C:36]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][O:46][C:47](=[O:50])[CH:48]=[CH2:49])=[CH:37][CH:38]=3)=[O:32])=[CH:26][C:23]=2[C:24]([OH:53])=[O:25])=[O:20])=[CH:17][CH:18]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 180AcetoneHCID 223924282,5-Di-[4-(6-acryloyloxyhexyloxy)benzoyloxy]benzaldehyde

Product 1

HCID 223924272,5-Di-[4-(6-acryloyloxyhexyloxy)benzoyloxy]benzoic acid

Procedure

Jones oxidant (CrO3/H2SO4/H2O) (48 ml) was added to a ice-cooled solution of 2,5-di-[4-(6-acryloyloxyhexyloxy)phenylcarbonyloxy]benzaldehyde (8.24 g, 12 mmol) in acetone (300 ml) in a dropwise fashion over a period of 30 min. The reaction mixture was stirred overnight at room temperature. The resulting green-orange mixture was filtered off to leave a green precipitate that was washed with 600 ml of ether. The combined organic solutions were washed with water until the orange coloration disappeared (6×250 ml). The colourless organic solution obtained was washed with saturated NaCl solution (2×300 ml), dried over MgSO4 and filtered. Removal of the solvent gave pure 2,5-di-[4-(6-acryloyloxyhexyloxy)phenylcarbonyloxy]benzoic acid as a white crystalline material. Yield 8.5 g.

Workup

  1. filtrationThe resulting green-orange mixture was filtered off
  2. customto leave a green precipitate that
  3. washwas washed with 600 ml of ether
  4. washThe combined organic solutions were washed with water until the orange coloration
  5. customThe colourless organic solution obtained
  6. washwas washed with saturated NaCl solution (2×300 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customRemoval of the solvent

Sources & evidence

ORD record
ord-d1ac90b1686746988a2142764a06bee4
Source dataset
uspto-grants-2004_06
Patent number
US06749771B1

Reaction notes

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