Heptanal → 1,1,1-Trichlorooctan-2-OL

HRID 2166672Notes

Reaction equation

HRID 2166672 reaction equation
C(=O)CCCCCC.ClC(Cl)(Cl)C([O-])=O.[Na+].C(=O)([O-])[O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:20]([Cl:23])([Cl:22])[Cl:21].[Na+]>O>[Cl:21][C:20]([Cl:22])([Cl:23])[CH:19]([OH:18])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 8130HeptanalHCID 23681045Sodium TrichloroacetateHCID 86737961Sodium 1,1,1-trichloro-2-octyl carbonate2×

Product 1

HCID 132384961,1,1-Trichlorooctan-2-OL

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The contents of a flask charged with n-heptanal (2.5 mmol), sodium trichloroacetate (2.7 mmol) and a solvent (10 g) were stirred for 16 hours. At the end of this period, when the reaction mixture contained sodium 1,1,1-trichloro-2-octyl carbonate (compound 24), ##STR35## water (50 ml) was added and the mixture was extracted with two portions (each of 25 ml) of n-pentane. Six experiments were thus carried out, each with another solvent. Table I shows which solvents and temperatures were used and presents the conversion of the n-heptanal and the selectivity to the title alcohol. These conversions and selectivities were already obtained after one hour stirring, stirring being continued overnight.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with two portions (each of 25 ml) of n-pentane
  3. customThese conversions and selectivities were already obtained after one hour
  4. stirringstirring

Sources & evidence

ORD record
ord-3a2440accaa34a75b62defb952bda42c
Source dataset
uspto-grants-1983_06
Patent number
US04388247

Reaction notes

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