2-Acetylhydroquinone → 6-Hydroxyspiro[2H-1-benzopyran-2,1′-cyclobutan]-4(3H)-one

HRID 453928Notes

Reaction equation

HRID 453928 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]1(=O)[CH2:15][CH2:14][CH2:13]1.N1CCCC1>>[OH:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[O:1][C:12]1([CH2:15][CH2:14][CH2:13]1)[CH2:10][C:9]2=[O:11]

Participants

4

Reactant 3

HCID 102792-AcetylhydroquinoneHCID 14496CyclobutanoneHCID 31268Pyrrolidine

Product 1

HCID 667463336-Hydroxyspiro[2H-1-benzopyran-2,1′-cyclobutan]-4(3H)-one

Procedure

The title compound was prepared from 2′,5′-dihydroxyacetophenone (10 g, 65.724 mmol) and cyclobutanone (13.29 ml, 131.44 mmol), in the presence of pyrrolidine (10.79 ml) by similar procedure as described in Step 1 of Intermediate 1 to give 10 g of the product; 1H NMR (300 MHz, CDCl3) δ 1.63-1.73 (m, 2H), 1.84-1.95 (m, 2H), 2.05-2.15 (m, 2H), 2.23-2.33 (m, 2H), 6.85 (d, J=8.7 Hz, 1H), 7.06 (d, J=9.0 Hz, 1H), 7.33 (s, 1H).

Sources & evidence

ORD record
ord-b17dd0d5b4304c6285f35546aac1c2d5
Source dataset
uspto-grants-2013_07
Patent number
US08492568B2

Reaction notes

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