(4-Nitrophenoxy)acetic acid → (4-Nitrophenoxy)acetyl chloride

HRID 1451633Notes

Reaction equation

HRID 1451633 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10](O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:17])=O>>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([Cl:17])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 15720(4-Nitrophenoxy)acetic acidHCID 24386Thionyl Chloride

Product 1

HCID 88380(4-Nitrophenoxy)acetyl chloride

Procedure

A mixture of (4-nitrophenoxy)acetic acid (50 g) and thionyl chloride (150 ml) was heated under reflux for 3 h. The solution was concentrated and then coevaporated with benzene to give 4-nitrophenoxyacetyl chloride as a solid. A solution of this solid (9.4 g) in acetone (100 ml) was added dropwise to a stirred mixture of 1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride (10 g) and sodium hydrogen carbonate (9 g) in acetone (100 ml) at 0°. Stirring was continued at room temperature for 16 h, the mixture was then filtered, and the filtrate was concentrated. The residue was treated with water and extracted with dichloromethane. The organic layer was washed with water, dried and concentrated to give the title compound (6.6 g) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-e52edaf67e604cc1bdcca2088a6272d6
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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