4-Chlororesorcinol → 5-chloro-6-hydroxybenzofuran-3(2H)-one

HRID 1749710Notes

Reaction equation

HRID 1749710 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9].[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH2:15][C:16](Cl)=[O:17].[OH-].[Na+]>[N+](C1C=CC=CC=1)([O-])=O>[Cl:1][C:2]1[C:3]([OH:9])=[CH:4][C:5]2[O:6][CH2:15][C:16](=[O:17])[C:7]=2[CH:8]=1

Participants

6

Reactant 4

HCID 17314-ChlororesorcinolHCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 574435495-chloro-6-hydroxybenzofuran-3(2H)-oneYield 18%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4-chlororesorcinol (4.34 g, 30.0 mmol) in nitrobenzene (60 mL) was added with aluminum chloride (10.2 g, 90.0 mmol) at room temperature. Then, the mixture was added with chloroacetyl chloride (2.87 mL, 36.0 mmol) under ice cooling. The mixture was stirred at 40° C. for 2 hours, and then added with 2 N aqueous sodium hydroxide (60 mL), and then the aqueous layer was separated. The separated aqueous layer was added with concentrated hydrochloric acid and thereby adjusted to pH 3, and the precipitated solid was collected by filtration to obtain the objective 5-chloro-6-hydroxybenzofuran-3(2H)-one (0.995 g, 17%).

Workup

  1. customthe aqueous layer was separated
  2. additionThe separated aqueous layer was added with concentrated hydrochloric acid
  3. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-5bf815f80cfc403bbd6608f3bdfe4340
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…