Acetic Acid → 4-(2-Methylphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta[g][1]benzopyran-3-carboxylic acid

HRID 36933Notes

Reaction equation

HRID 36933 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]2[CH:14]=[C:15]3[CH2:20][CH2:19][CH2:18][C:16]3=[CH:17][C:12]=2[O:11][C:10](=[O:21])[C:9]=1[C:22]([O:24]CC)=[O:23].Cl.C(O)(=O)C>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]2[CH:14]=[C:15]3[CH2:20][CH2:19][CH2:18][C:16]3=[CH:17][C:12]=2[O:11][C:10](=[O:21])[C:9]=1[C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 10450416HCID 10450416, compound

Product 1

HCID 103586304-(2-Methylphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta[g][1]benzopyran-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 4-(2-methylphenyl)-2-oxo -2,6,7,8-tetrahydrocyclopenta[g][1]benzopyran-3-carboxylate (5.0 g), concentrated hydrochloric acid (13 ml) and acetic acid (25 ml) was refluxed for 12 hours. To this reaction mixture was added water, whereupon 4-(2-methylphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta [g][1]benzopyran-3-carboxylic acid was obtained as crystals (4.5 g, 97.8%). Recrystallization from acetone-hexane gave colorless prisms, mp 213°-214° C.

Workup

  1. temperaturewas refluxed for 12 hours

Sources & evidence

ORD record
ord-753534e75e094266bc7ffdb3e67a53eb
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Reaction notes

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