Carbon Disulfide → HCID 13302038, compound

HRID 1709006Notes

Reaction equation

HRID 1709006 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:23](=[S:25])=[S:24].[OH-].[K+].Cl[CH2:29][CH2:30][CH2:31]Cl>CS(C)=O.O.CCCCCC>[S:24]1[CH2:31][CH2:30][CH2:29][S:25][C:23]1=[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:21])([F:22])[F:1])[CH:4]=1)[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:11]

Participants

8

Reactant 4

HCID 6348Carbon DisulfideHCID 88811,3-DichloropropaneHCID 14797Potassium HydroxideHCID 13302037Octyl [3-(trifluoromethyl)phenyl]acetate

Product 1

HCID 13302038HCID 13302038, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of n-octyl 3-trifluoromethylphenylacetate (112.2 g) in dimethyl sulphoxide (850 ml) there are added carbon disulphide (30.4 g) and, slowly, a solution of potassium hydroxide (60.0 g) in water (100 ml). The mixture is stirred for 2 hours at 40°. 1,3-dichloropropane (40.1 g) is then added and the mixture is stirred at 50° for 3 hours. Water (800 ml) and hexane (800 ml) are added, the two phases are separated and the aqueous solution is extracted with hexane (2×500 ml). The combined organic phases are washed with water (400 ml), dried over magnesium sulphate and evaporated. The residue is crystallized from pentane. The product is dried in vacuo to constant weight to yield n-octyl (1,3-dithian-2-ylidene)-(3-trifluoromethylphenyl)-acetate, m.p. 49° (as Example 11).

Workup

  1. stirringthe mixture is stirred at 50° for 3 hours
  2. customthe two phases are separated
  3. extractionthe aqueous solution is extracted with hexane (2×500 ml)
  4. washThe combined organic phases are washed with water (400 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue is crystallized from pentane
  8. customThe product is dried in vacuo to constant weight

Sources & evidence

ORD record
ord-c92aa8d19d8b4825a550506975fc81dc
Source dataset
uspto-grants-1990_08
Patent number
US04946861

Reaction notes

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