Heptanal → 1,1,1-Trichlorooctan-2-OL

HRID 1659829Notes

Reaction equation

HRID 1659829 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-4e8e2c40d5dd4e2098050f58fc122a5b
Source dataset
uspto-grants-1981_12
Patent number
US04305890

Reaction notes

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