p-Toluenesulfonic acid → HCID 20229920, compound

HRID 2290692Notes

Reaction equation

HRID 2290692 reaction equation
[O:1]1[CH:5]=[CH:4][CH2:3][CH2:2]1.[N+:6]([C:9]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=2[Cl:29])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])([O-:8])=[O:7].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[N+:6]([C:9]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][C:20]=2[Cl:29])=[CH:14][C:10]=1[C:11]([O:13][CH:5]1[CH2:4][CH2:3][CH2:2][O:1]1)=[O:12])([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 44073AcifluorfenHCID 709342,3-Dihydrofuran

Product 1

HCID 20229920HCID 20229920, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dihydrofuran (0.03 mole), 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid (0.025 mole), methylene chloride (25 ml) and p-toluenesulfonic acid (1 spatula tip) are charged into a glass reaction vessel equipped with a magnetic stirrer. The reaction mixture is stirred at room temperature until the carboxylic acid group can no longer be detected by IR in the mixture. After this time, the reaction mixture is washed with dilute aqueous sodium carbonate and with water. The washed solution was dried and stripped of solvent and unreacted starting material to yield the desired product 2-tetrahydrofuryl 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoate.

Workup

  1. customequipped with a magnetic stirrer
  2. washAfter this time, the reaction mixture is washed with dilute aqueous sodium carbonate and with water
  3. customThe washed solution was dried

Sources & evidence

ORD record
ord-1011c5b5c4b14bfd89111bd4268d8135
Source dataset
uspto-grants-1986_10
Patent number
US04618359

Reaction notes

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