2-Acetylhydroquinone → HCID 14329708, compound

HRID 2232477Notes

Reaction equation

HRID 2232477 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[C:12]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:13][CH2:14][C:15]([CH3:17])=O.N1CCCC1>C1(C)C=CC=CC=1>[CH2:20]([O:19][C:12](=[O:18])[CH2:13][CH2:14][C:15]1([CH3:17])[CH2:10][C:9](=[O:11])[C:3]2[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=2[O:1]1)[CH3:21]

Participants

5

Reactant 3

HCID 102792-AcetylhydroquinoneHCID 10883Ethyl levulinateHCID 31268Pyrrolidine

Product 1

HCID 14329708HCID 14329708, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Using the procedure of Example 1, 15 g of 2',5'-dihydroxyacetophenone was condensed with 14.2 g of ethyl levulinate and 12.3 ml of pyrrolidine, in 200 ml of toluene. The crude product (20.5 g) was purified by high pressure liquid chromatography (silica gel; 2:1 hexane-ethyl acetate) giving 17.6 g (64.1%) of racemic-3,4-dihydro-6-hydroxy-2-methyl-4-oxo-2H-1-benzopyran-2-propanoic acid ethyl ester was a yellow oil.

Workup

  1. customThe crude product (20.5 g) was purified by high pressure liquid chromatography (silica gel; 2:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2cc7f5381d0f4d0fb64a9b2bfe2568b9
Source dataset
uspto-grants-1988_11
Patent number
US04788214

Reaction notes

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