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

HRID 904587Notes

Reaction equation

HRID 904587 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. 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 three 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 three times with ether (200 ml
  2. customeach), dried
  3. customthe ether removed

Sources & evidence

ORD record
ord-bac1be8dd6b244bf808ae80922be4d33
Source dataset
uspto-grants-1983_12
Patent number
USRE031455

Reaction notes

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