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

HRID 1873142Notes

Reaction equation

HRID 1873142 reaction equation
[Cl: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+].O.Cl>O1CCOCC1>[Cl: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 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15481263Methanesulfonic acid 4-(6-Chloro-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenyl ester

Product 1

HCID 154812674-(6-Chloro-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenolYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A biphasic mixture of methanesulfonic acid 4-(6-chloro-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenyl ester (0.917 g, 2.09 mmol) in dioxane (13 mL) and a solution of sodium hydroxide (2.5 N, 6.7 mL, 16.7 mmol, 8 eq) was heated at reflux overnight. After cooling to room temperature the reaction mixture was combined with water (50 mL), acidified with concentrated hydrochloric acid, and stirred for 15 minutes. The crude white solid product was collected by filtration, redissolved in ether, combined with silica gel, and the solvent was removed. The adsorbate was flash chromatographed (gradient 85/15-80/20 petroleum ether/ethyl acetate) to give the title compound as a white solid (0.705 g, 94%); mp 193-195° C.; NMR (CDCl3); δ 8.37 (ddd, J=8, 1, Hz, 1H), 7.81 (ddd, J=8, 1, 1 Hz, 1H), 7.68-7.63 (m, 2H), 7.44 (ddd, J=8, 7, 1 Hz, 1H), 7.39 (ddd, J=8, 7, 1 Hz, 1H), 7.29-7.26 (m, 2H,), 7.14-7.09 (m, 3H), 6.81 (ddd, J=8, 1, 1 Hz, 1H), 5.01 (d, J=4 Hz, 1H); MS (+EI): [M+], 1 chlorine isotope pattern, 360 (100%), 362 (45%); Anal. calc. for C22H13ClOS: C, 73.23, H, 3.63, N, 0.00. Found: C, 72.86, H, 3.24, N, 0.04.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe crude white solid product was collected by filtration
  3. dissolutionredissolved in ether
  4. customthe solvent was removed
  5. customchromatographed (gradient 85/15-80/20 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-80c0251de3264b32a8e979d7c064c2ad
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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