Hydrochloric Acid → HCID 18430083, compound

HRID 1280247Notes

Reaction equation

HRID 1280247 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([Cl:24])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](OCC)=[O:10].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([Cl:24])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 18430009HCID 18430009, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18430083HCID 18430083, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-70 °C

Procedure

To a mixture of 4.06 g of ethyl 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)valerate and 50 ml of toluene was added dropwise 10.27 ml of 0.95 mol/liter diisobutyl aluminum hydride (hexane solution) over 30 minutes with stirring at −70° C. in a stream of nitrogen gas. After further stirring at −70° C. for 1 hour, 50 ml of saturated aqueous ammonium chloride solution was added. The reaction mixture was returned to room temperature, and poured into 50 ml of diluted hydrochloric acid, and extracted twice with toluene. The toluene layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated, which afforded 3.52 g (yield, 96%) of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentanal.

Workup

  1. stirringAfter further stirring at −70° C. for 1 hour
  2. customwas returned to room temperature
  3. extractionextracted twice with toluene
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-64121cf8249e42e5ac2723bdcc0b20a0
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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