Acetic Acid → HCID 53731949, compound

HRID 362443Notes

Reaction equation

HRID 362443 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[C:9]([Cl:30])[CH:8]=1)C.Cl.C(O)(=O)C>O>[F:29][C:26]([F:27])([F:28])[C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:10]2[C:9]([Cl:30])=[CH:8][C:7]([O:6][CH2:5][CH:4]=[O:3])=[CH:12][C:11]=2[Cl:13])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 54318048HCID 54318048, compound

Product 1

HCID 53731949HCID 53731949, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(4-(4-(Trifluoromethyl)phenoxy)butyloxy)-3,5-dichlorophenoxyacetaldehyde diethylacetal (manufactured in Production Example 1 of intermediate described hereinafter) (1.0 g) was added dropwise to a mixed solution of 1 ml of hydrochloric acid and 9 ml of acetic acid with stirring at room temperature. After stirring at room temperature for 20 minutes, the reaction solution was poured into iced water and extracted twice with 100 ml of diethyl ether. The ether layers were combined, washed with water, washed twice with aqueous 5% sodium hydrogencarbonate, washed with water, dried over anhydrous magnesium sulfate and then concentrated to obtain 0.7 g of 4-(4-(4-(trifluoromethyl)phenoxy)butyloxy)-3,5-dichlorophenoxyacetaldehyde as a crude product.

Workup

  1. stirringAfter stirring at room temperature for 20 minutes
  2. extractionextracted twice with 100 ml of diethyl ether
  3. washwashed with water
  4. washwashed twice with aqueous 5% sodium hydrogencarbonate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5ef300d3c3e549bdaab243999a7ac9e3
Source dataset
uspto-grants-1999_02
Patent number
US05869506

Reaction notes

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