Hydrochloric Acid → 4-(6-Iodo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenol

HRID 1873143Notes

Reaction equation

HRID 1873143 reaction equation
[I:1][C:2]1[C:14]2[S:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10]=2[C:9]([C:19]2[CH:24]=[CH:23][C:22]([O:25]S(C)(=O)=O)=[CH:21][CH:20]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[OH-].[Na+].Cl>O1CCCC1.O>[I:1][C:2]1[C:14]2[S:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10]=2[C:9]([C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15481264Methanesulfonic acid 4-(6-Iodo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenyl ester

Product 1

HCID 154812684-(6-Iodo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenolYield 101.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methanesulfonic acid 4-(6-iodo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenyl ester (1.00 g, 1.89 mmol) in tetrahydrofuran (5 mL) was added a 2.5 N aqueous solution of sodium hydroxide (6.0 mL) and the biphasic reaction mixture was heated at reflux for 5 hours and then heated in a sealed pressure tube at 110 C. for about 18 hours. The reaction mixture was diluted with water (100 mL), acidified with 10% hydrochloric acid and the organics were extracted with ether (2×100 mL). The extracts were combined, washed with water (100 mL), concentrated and chased with petroleum ether to give the title compound (0.869 g, over theoretical); NMR (DMSO-d6); δ 9.85 (s, 1H, OH), 8.15 (d, J=8 Hz, 1H), 8.02 (d, J=8 Hz, 1H), 7.73 (ddd, J=8, 7, 1 Hz, 1H), 7.69-7.44 (m, 3H), 7.21-7.16 (m, 3H), 7.09-7.06 (m, 2H), 6.68 (d, J=8Hz, 1H).

Workup

  1. customthe biphasic reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 5 hours
  4. temperatureheated in a sealed pressure tube at 110 C
  5. extractionthe organics were extracted with ether (2×100 mL)
  6. washwashed with water (100 mL)
  7. concentrationconcentrated and chased with petroleum ether

Sources & evidence

ORD record
ord-78b6d546b701422fb8f522939b0bb420
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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