Hydroquinone → 4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid

HRID 1655817Notes

Reaction equation

HRID 1655817 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1.[C:18](O)(=[O:21])[CH:19]=[CH2:20].S(=O)(=O)(O)O.C1(C=CC(O)=CC=1)O>C1C=CC=CC=1>[C:18]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:16][CH:17]=1)(=[O:21])[CH:19]=[CH2:20]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 6581Acrylic AcidHCID 36284134-(6-Hydroxyhexyloxy)benzoic acid

Product 1

HCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidYield 55%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4.8 g of 4-(6-hydroxyhexyloxy)benzoic acid and 5.8 g of acrylic acid were heat-refluxed for 40 hours together with 1 ml of sulfuric acid in the presence of hydroquinone in benzene, followed by distilling-off of the solvent and recrystallization to obtain 3.2 g of the product. (Yield: 55 %)

Workup

  1. customfollowed by distilling-off of the solvent and recrystallization

Sources & evidence

ORD record
ord-61408abb5d7043ac95f741c90f3ced53
Source dataset
uspto-grants-1993_10
Patent number
US05252251

Reaction notes

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