Carbonic Acid → 4-{[12-(Acryloyloxy)dodecyl]oxy}benzoic acid

HRID 2072639Notes

Reaction equation

HRID 2072639 reaction equation
[OH:1][C:2]([OH:4])=O.[C:5]([OH:9])(=[O:8])[CH:6]=[CH2:7].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13](S(O)(=O)=O)=[CH:12][CH:11]=1.[C:21]1([CH:28]=[CH:27][C:25]([OH:26])=[CH:24][CH:23]=1)O>C(Cl)(Cl)Cl.CCOCC>[C:5]([O:9][CH2:12][CH2:11][CH2:10][CH2:15][CH2:14][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:10][CH2:20][O:26][C:25]1[CH:27]=[CH:28][C:21]([C:2]([OH:4])=[O:1])=[CH:23][CH:24]=1)(=[O:8])[CH:6]=[CH2:7]

Participants

7

Reactant 4

HCID 767Carbonic AcidHCID 785HydroquinoneHCID 6101p-Toluenesulfonic acidHCID 6581Acrylic Acid

Product 1

HCID 197890084-{[12-(Acryloyloxy)dodecyl]oxy}benzoic acidYield 1,982%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

A solution of 50 m moles (15.9 g) of the above hydroxycarboxylic acid, 0.6 mole (43.2 g) of acrylic acid, 0.3 g of p-toluenesulfonic acid, and 0.3 g of hydroquinone in 30 ml of chloroform was refluxed for 30 hours. The reaction solution was disolved in warm ether, and washed with warm water, then concentrated. The concentrate was purified by column chromatography to obtain 6.5 g of the ester compound. (yield: 35%)

Workup

  1. washwashed with warm water
  2. concentrationconcentrated
  3. customThe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-87a0bbdcb6154ff9961f9f3d6f61191a
Source dataset
uspto-grants-1990_04
Patent number
US04913839

Reaction notes

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