Toluene → 2,3-Dihydro-6-Methoxy-2-(4-Methoxyphenyl)benzo[b]thiophene-3-Carboxylic Acid

HRID 850721Notes

Reaction equation

HRID 850721 reaction equation
C[O:2][C:3]([CH:5]1[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[S:8][C:7]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:6]1=2)=[O:4].[OH-].[Na+].C1(C)C=CC=CC=1>CO.O.C(OCC)C>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:6]2[CH:5]([C:3]([OH:4])=[O:2])[CH:9]([C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)[S:8][C:7]=2[CH:18]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 14798Sodium Hydroxide2×HCID 154582622,3-Dihydro-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxylic acid methyl ester

Product 1

HCID 154582642,3-Dihydro-6-Methoxy-2-(4-Methoxyphenyl)benzo[b]thiophene-3-Carboxylic AcidYield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2,3-dihydro-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxylic acid methyl ester (0.7337 g, 2.21 mmol) in methanol (10 ml) at 5° C. was added 5 N sodium hydroxide (1 ml, 5 mmol) and water (5 ml). The resulting slurry was stirred at that temperature for 1 hour, then toluene (5 ml) was added, and the resulting mixture was stirred at room temperature for 16 hours. Additional 5 N sodium hydroxide (1 ml) was then added, and the mixture stirred an additional 16 hours. The reaction mixture was then diluted with water (5 ml) and diethyl ether (20 ml), and the layers separated. The aqueous layer was acidified to pH 1 with 1 N hydrochloric acid, and extracted with diethyl ether (2×50 ml). The ether layers were combined, dried (magnesium sulfate), filtered and concentrated to a foam, which was further dried in vacuo to afford 0.6146 g (88%) of title compound. IR (KBr) 3300-2800 (br), 2836, 1710, 1611, 1594, 1514, 1482, 1248, 1181, 1030 cm-1 ; 1H NMR (CDCl3): δ11.63 (br s, 1 H), 7.37 (d, 2 H, J=8.4 Hz); 7.24 (d, 1 H, J=8.4 Hz), 6.85 (d, 2 H, J=8.4 Hz), 6.78 (d, 1 H, J=2.2 Hz), 6.67 (dd, 1 H, J=8.4, 2.2 Hz), 5.38 (d, 1 H, J=7.5 Hz), 4.42 (d, 1 H, J=7.5 Hz), 3.79 (s, 6 H); 13C NMR (CDCl3): d 177.7, 160.7, 159.5, 142.8, 132.3, 128.7, 127.3, 126.0, 114.3, 111.0, 107.5, 60.3, 55.6, 55.4, 55.1. Anal. calcd. for C17H16O4S: C, 64.54; H, 5.10; S; 10.13. Found: C, 64.78; H, 5.14; S, 10.55.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 16 hours
  2. stirringthe mixture stirred an additional 16 hours
  3. customthe layers separated
  4. extractionextracted with diethyl ether (2×50 ml)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated to a foam, which
  8. customwas further dried in vacuo

Sources & evidence

ORD record
ord-ba01d915adf14daeb25561a98f150f14
Source dataset
uspto-grants-2000_01
Patent number
US06018056

Reaction notes

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