Hydroquinone → 5-Hydroxy-2-oxo-3-(2,5-dimethylphenyl)-2,3-dihydrobenzofuran

HRID 862188Notes

Reaction equation

HRID 862188 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[CH:4](O)[C:5]([OH:7])=[O:6].[C:14]1([CH:21]=[CH:20][C:18](O)=[CH:17][CH:16]=1)[OH:15].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[OH:15][C:14]1[CH:16]=[CH:17][C:18]2[O:7][C:5](=[O:6])[CH:4]([C:3]3[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:2]=3[CH3:1])[C:20]=2[CH:21]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 2776622-(2,5-Dimethylphenyl)-2-hydroxyacetic acid

Product 1

HCID 197022995-Hydroxy-2-oxo-3-(2,5-dimethylphenyl)-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

By the method described in GB 2068402A 2,5-dimethylmandelic acid (65 parts) was reacted with hydroquinone (33 parts) and 98% sulfuric acid (32 parts) and toluene (440 parts) to give 5-hydroxy-2-oxo-3-(2,5-dimethylphenyl)-2,3-dihydrobenzofuran (33 parts) which was isolated by crystallisation and chromatography. The 1Hnmr spectrum of the purified product was consistent with structure.

Sources & evidence

ORD record
ord-3c795f349829419ca0fa525f12fc2d75
Source dataset
uspto-grants-1998_02
Patent number
US05717112

Reaction notes

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