Hydroquinone → 4-(4-acryloxybutoxy)benzoic acid

HRID 355598

Reaction equation

HRID 355598 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.[C:16](O)(=[O:19])[CH:17]=[CH2:18].C1(C=CC(O)=CC=1)O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC(Cl)(Cl)C>[C:16]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)(=[O:19])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 6101p-Toluenesulfonic acidHCID 6581Acrylic AcidHCID 152185964-(4-Hydroxybutoxy)benzoic acid

Product 1

HCID 110327354-(4-acryloxybutoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 62781,1,1-TrichloroethaneSolvent

Procedure

A solution of (1) (282 g; 1.34 mol), freshly distilled acrylic acid (230 ml; 3.35 mol), hydroquinone (1.9 g) and p-toluenesulfonic acid (23.7 g) in 1,1,1-trichloroethane (1.1 l) is refluxed for 10 hours. The reaction mixture is cooled to from 60° to 70° C. and stirred into 2.5 l of petroleum ether, and the precipitate is filtered off, washed with petroleum ether and dried at room temperature under reduced pressure for 24 hours.

Workup

  1. temperatureThe reaction mixture is cooled to from 60° to 70° C.
  2. filtrationthe precipitate is filtered off
  3. washwashed with petroleum ether
  4. customdried at room temperature under reduced pressure for 24 hours

Sources & evidence

ORD record
ord-2ec6ac0b8cc247aa84856d01f6ecf9ff
Source dataset
uspto-grants-1998_11
Patent number
US05833880

Linked notes

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