Itaconic acid → HCID 67988894, compound

HRID 1428994Notes

Reaction equation

HRID 1428994 reaction equation
[C:1]1(C)C=CC=C[CH:2]=1.[C:8]1([CH:15]=[CH:14][CH:13]=[C:11]([OH:12])[CH:10]=1)[OH:9].[C:16]([OH:24])(=O)[C:17]([CH2:19][C:20]([OH:22])=[O:21])=[CH2:18]>CCCCCC.C(OCC)(=O)C>[OH:9][C:8]1[CH:10]=[C:11]2[C:13]([CH2:18][CH:17]([CH2:19][C:20]([O:22][CH2:1][CH3:2])=[O:21])[C:16](=[O:24])[O:12]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 811Itaconic acidHCID 1140TolueneHCID 5054Resorcinol

Product 1

HCID 67988894HCID 67988894, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

100 ml of toluene were admixed with 4.4 g (0.04 mol) of resorcinol and 6.32 g (0.04 mol) of the ethyl monoester of itaconic acid, and also 8.8 g of Amberlyst 15 resin from Aldrich. The reaction mixture was stirred for 2 hours and then filtered off to cooling. The filtrate was concentrated and purified by flash chromatography on a silica column (eluent CH2Cl2: MeOH=50:1), to give, following recrystallization from a 3/1 hexane/ethyl acetate mixture, 4.6 g (46% yield) of the expected lactone C2 in the form of a white solid.

Workup

  1. filtrationfiltered off
  2. temperatureto cooling
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography on a silica column (eluent CH2Cl2: MeOH=50:1)
  5. customto give

Sources & evidence

ORD record
ord-eb03237af2a34f2e9e94c5887df5dd74
Source dataset
uspto-grants-2015_01
Patent number
US08937187B2

Reaction notes

Loading…