Hydroquinone → HCID 22167616, compound

HRID 2245906Notes

Reaction equation

HRID 2245906 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].O[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:24]([OH:26])=[O:25])[CH:18]=[CH:17]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O>ClCCCl>[C:1]([O:5][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:24]([OH:26])=[O:25])[CH:18]=[CH:17]2)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 6581Acrylic AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 22167614HCID 22167614, compound

Product 1

HCID 22167616HCID 22167616, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In 270 g of 1,2-dichloroethane were added 108.11 g (1.5 mmol) of acrylic acid, 21.63 g (75 mmol) of 6-(6-hydroxy-hexa-1-yloxy)-2-naphthoic acid obtained in Step 1, 4.28 g (23 mol) of p-toluenesulfonic acid monohydrate, and 0.83 g (7.5 mmol) of hydroquinone, and the solution was refluxed for 4 hours. After evaporation of the solvent, 270 g of water was added to the residue, and the precipitate was collected by filtration and dried in an oven at 40° C. overnight. The dried product was recrystallized from acetone to yield the desired product, 6-(6-acryloyloxy-hexa-1-yloxy)-2-naphthoic acid, as light-yellow powder (16.97 g, Yield: 65%).

Workup

  1. temperaturethe solution was refluxed for 4 hours
  2. customAfter evaporation of the solvent, 270 g of water
  3. additionwas added to the residue
  4. filtrationthe precipitate was collected by filtration
  5. customdried in an oven at 40° C. overnight
  6. customThe dried product was recrystallized from acetone

Sources & evidence

ORD record
ord-c752226c42b84707b68ad5df33e9cbed
Source dataset
uspto-grants-2010_03
Patent number
US07683203B2

Reaction notes

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