2-Chloroethanol → HCID 10976708, compound

HRID 1198755Notes

Reaction equation

HRID 1198755 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[C:6]([CH2:8][C:9](OCC)=O)=[O:7])([O-:3])=[O:2].ClC[CH2:20][OH:21].[OH-].[Na+].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O>[OH:21][CH2:20][CH2:9][CH2:8][C:6]([C:5]1[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=1[N+:1]([O-:3])=[O:2])=[O:7]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxideHCID 10561837Ethyl 2-nitro-beta-oxobenzenepropanoate

Product 1

HCID 10976708HCID 10976708, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-(o-nitrobenzoyl)acetate (11.9 g, 0.05 mol), 2-chloroethanol (8 g, 0.1 mol), 50% sodium hydroxide solution (8.8 g, 4.4 g real, 0.11 mol) and 40% benzyltrimethylammonium hydroxide solution (4.2 PG,12 g, 1.7 g, real, 0.01 mol) in water (50 mL) is heated at 50°-65° C. for 4-8 hours, cooled and extracted with methylene chloride. The combined organic extracts are concentrated in vacuo to give the title product, identified by 1HNMR and 13CNMR analyses.

Workup

  1. temperatureis heated at 50°-65° C. for 4-8 hours
  2. temperaturecooled
  3. extractionextracted with methylene chloride
  4. concentrationThe combined organic extracts are concentrated in vacuo

Sources & evidence

ORD record
ord-f67cba12d1774568ba0a99d4ef24dae6
Source dataset
uspto-grants-1994_01
Patent number
US05281726

Reaction notes

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