Acetic Acid → HCID 54234953, compound

HRID 1280244Notes

Reaction equation

HRID 1280244 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([O:25][CH2:26][CH:27]=[C:28]([Cl:30])[Cl:29])[CH:6]=[C:7]([CH2:23][CH3:24])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16](OCC)[O:17]CC)[CH3:2].C(O)(=O)C.Cl>O>[CH2:23]([C:7]1[CH:6]=[C:5]([O:25][CH2:26][CH:27]=[C:28]([Cl:29])[Cl:30])[CH:4]=[C:3]([CH2:1][CH3:2])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]=[O:17])[CH3:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 184299913,5-Diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2,2-diethoxyethoxy)butyloxy)benzene

Product 1

HCID 54234953HCID 54234953, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 9.27 g of 3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(4-(2,2-diethoxyethoxy)butyloxy)benzene, 25 ml of acetic acid, and 5 ml of water was added 1 ml of concentrated hydrochloric acid at room temperature. After stirring at room temperature for 30 minutes, the reaction mixture was poured into water, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, aqueous sodium hydrogencarbonate solution, and aqueous sodium chloride solution in this order, dried over anhydrous magnesium sulfate, and concentrated, which afforded 7.62 g (yield, 98%) of 4-(2,6-diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde.

Workup

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

Sources & evidence

ORD record
ord-7c11b9eade8348948abb9211a2788666
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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