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

HRID 65327Notes

Reaction equation

HRID 65327 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-0bf12878d0a24049ad66a1398689adf3
Source dataset
uspto-grants-1986_09
Patent number
US04613360

Reaction notes

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