Acetic Acid → 4-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde

HRID 369688

Reaction equation

HRID 369688 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:23][CH2:24][CH:25]=[C:26]([Cl:28])[Cl:27])[CH:5]=[C:6]([Cl:22])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH:15](OCC)[O:16]CC.C(O)(=O)C.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([O:23][CH2:24][CH:25]=[C:26]([Cl:28])[Cl:27])[CH:5]=[C:6]([Cl:22])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH:15]=[O:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 184293933,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2,2-diethoxyethoxy)butyloxy)benzene

Product 1

HCID 538269084-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehydeYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 1.81 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2,2-diethoxyethoxy)butyloxy)benzene was added to a mixture of 10 ml of acetic acid and 1 ml of concentrated hydrochloric acid with stirring under ice cooling. After further stirring for 15 minutes, the reaction mixture was poured into water and extracted twice with diethyl ether. The diethyl ether layers were combined and washed with water, aqueous sodium hydrogencarbonate solution and then saturated sodium chloride solution. The combined diethyl ether layer was dried over magnesium sulfate, and the diethyl ether was distilled out, which afforded 1.51 g of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-butyloxyacetaldehyde (yield, 94%).

Workup

  1. stirringAfter further stirring for 15 minutes
  2. extractionextracted twice with diethyl ether
  3. washwashed with water, aqueous sodium hydrogencarbonate solution
  4. dry with materialThe combined diethyl ether layer was dried over magnesium sulfate
  5. distillationthe diethyl ether was distilled out

Sources & evidence

ORD record
ord-ff03748e3fd349718a22b40499543d59
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Linked notes

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