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

HRID 1280240Notes

Reaction equation

HRID 1280240 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

Then, 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, and the stirring was further continued for 15 minutes. The reaction mixture was poured into water, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, saturated aqueous sodium hydrogencarbonate solution, and saturated aqueous sodium chloride solution in this order, dried over anhydrous magnesium sulfate, and concentrated, which afforded 1.51 g (yield, 94%) of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde.

Workup

  1. extractionextracted twice with diethyl ether
  2. washwashed with water, saturated aqueous sodium hydrogencarbonate solution, and saturated aqueous sodium chloride solution in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c289f864a13f4712ada0a7d158f43fa8
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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