1-Butanol → Benzenepropanol

HRID 1153886

Reaction equation

HRID 1153886 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].ClCl.Cl[CH:9](Cl)[CH:10](Cl)Cl.Cl[C:15](Cl)([CH2:18]C)[CH:16]=O>CN(C=O)C.Cl.C(O)C(C)C>[C:4]1([CH2:3][CH2:2][CH2:1][OH:5])[CH:10]=[CH:9][CH:18]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 65911,1,2,2-TetrachloroethaneHCID 24526ChlorineHCID 112750512,2-Dichlorobutanal

Product 1

HCID 31234Benzenepropanol

Reagents, catalysts & solvents 2

HCID 10920465N,N-dimethylformamide;hydrochlorideCatalystHCID 6560IsobutanolSolvent

Procedure

n-Butanol and Cl2 were added concurrently to a 100 ml, four necked, round bottomed flask containing ~10 g of DMF/HCl catalyst and 25 ml of 1,1,2,2-tetrachloroethane. The temperature was maintained between 50° and 55° C. by controlling the rates of the addition. Upon completion of the addition, the reaction mixture was shown to contain mainly the product 2,2-dichlorobutyraldehyde by GC and NMR analysis. Similar results were obtained with isobutanol and 3-phenylpropanol. Analysis was in agreement with authentic products by GC, IR and NMR.

Workup

  1. temperatureThe temperature was maintained between 50° and 55° C.
  2. additionthe rates of the addition
  3. additionUpon completion of the addition
  4. customSimilar results

Sources & evidence

ORD record
ord-58577cdad3b14dbdae74e7181a87f133
Source dataset
uspto-grants-1984_12
Patent number
US04486608

Linked notes

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