Ethanol → 2-Chloro-alpha,alpha,alpha-trifluoro-p-tolyl-3-(1-carboxyethoxy)-4-nitrophenyl ether

HRID 1979646Notes

Reaction equation

HRID 1979646 reaction equation
[Cl:1][C:2]1[CH:7]([O:8][CH:9]([C:11]([O:13]CC)=[O:12])[CH3:10])[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:28])([F:27])[F:26])([N+:16]([O-:18])=[O:17])[CH:5]=[CH:4][C:3]=1[O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:46]([O-:48])=[O:47])([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]([F:45])([F:44])[F:43])[CH:32]([O:49][CH:50]([C:52]([O:54]CC)=[O:53])[CH3:51])[C:31]=1[Cl:57].[OH-].[K+].C(O)C.S(=O)(=O)(O)O>O.CCOCC.O1CCOCC1>[Cl:1][C:2]1[CH:7]([O:8][CH:9]([C:11]([OH:13])=[O:12])[CH3:10])[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:28])([F:27])[F:26])([N+:16]([O-:18])=[O:17])[CH:5]=[CH:4][C:3]=1[O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:46]([O-:48])=[O:47])([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]([F:45])([F:44])[F:43])[CH:32]([O:49][CH:50]([C:52]([OH:54])=[O:53])[CH3:51])[C:31]=1[Cl:57]

Participants

8

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 867350572-Chloro-alpha,alpha,alpha-trifluoro-p-tolyl-3-(1-carbethoxyethoxy)-4-nitrophenyl ether

Product 1

HCID 867350562-Chloro-alpha,alpha,alpha-trifluoro-p-tolyl-3-(1-carboxyethoxy)-4-nitrophenyl etherYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-α,α,α-trifluoro-p-tolyl-3-(1-carbethoxyethoxy)-4-nitrophenyl ether (8.6 g. of 0.02 mol), potassium hydroxide 86% (2.6 g. 0.04 mol), ethanol (8 ml.), dioxane (8 ml.) and water (100 ml.) are heated at 90°-95° C. for 30 minutes. Ether (200 ml.) and water (200 ml.) are added and the mixture acidified with dilute sulfuric acid, the water layer extracted 3 times with ether (200 ml. each), dried, and the ether removed to give 2-chloro-α,α,α-trifluoro-p-tolyl-3-(1-carboxyethoxy)-4-nitrophenyl ether (6.4 g. 79%) m.p. 108°-109° C.

Workup

  1. extractionthe water layer extracted 3 times with ether (200 ml
  2. customeach), dried
  3. customthe ether removed

Sources & evidence

ORD record
ord-d9c06b5fe11b4b2bad1295ebfb248dc6
Source dataset
uspto-grants-1984_11
Patent number
USRE031731

Reaction notes

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