1,1,2-Trichloroethane → HCID 54150769, compound

HRID 851815Notes

Reaction equation

HRID 851815 reaction equation
C1(S([CH2:10][CH2:11][CH2:12][CH:13]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=O)(=O)=O)C=CC=CC=1.C1(S)C=CC=CC=1.C(Cl)C(Cl)Cl.C(OO)(=O)C.OS([O-])=O.[Na+].[OH-].[Na+]>O>[C:13]12[CH2:12][CH2:11][CH:10]=[C:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=2

Participants

8

Reactant 6

HCID 65741,1,2-TrichloroethaneHCID 6585Peracetic AcidHCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 205012032-[3-(Benzenesulfonyl)propyl]cyclododecan-1-oneHCID 23665763Sodium Bisulfite

Product 1

HCID 54150769HCID 54150769, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(3-Phenylsulfonyl-prop-1-yl)-cyclododecanone used hereinabove (Examples 1 and 2) as starting material was prepared as follows: 222 g (1 mole) of 2-allyl-cyclododecanone-Helv. 54, 2889 (1971)--in admixture with 132 g (1.2 mole) of thiophenol and 3.0 g of α,α'-azoisobutyronitrile were heated at 100° for 10 hours, an additional amount of 6.0 g of α,α'-azoisobutyronitrile being added over this period, portionwise, to the reaction mixture. After dilution with an excess amount of trichloroethane and cooling in an ice-bath, 376 ml (2.6 mole) of 40% peracetic acid were progressively added to the reaction mixture, under good stirring (reaction temperature: 25°-30°). After treatment with an excess amount of an aqueous solution of NaHSO3 (elimination of peroxides), a 10% solution of NaOH in water was added thereto until pH 8-9 (temperature ca. 10°). After extraction with methylene chloride (2×300 ml), successive washings with water and brine, drying over Na2SO4, evaporation and crystallization of the crude residue in a CH2Cl2 /diethyl ether/petrol ether mixture, there were finally isolated 332 g (91% yield) of the desired compound, m.p. 97°-102°.

Workup

  1. customwas prepared
  2. custom(reaction temperature: 25°-30°)
  3. customuntil pH 8-9 (temperature ca. 10°)
  4. extractionAfter extraction
  5. washwith methylene chloride (2×300 ml), successive washings with water and brine
  6. dry with materialdrying over Na2SO4, evaporation and crystallization of the crude residue in a CH2Cl2 /diethyl ether/petrol ether mixture, there

Sources & evidence

ORD record
ord-35b7bb0bbb904cd8b830e16b038a239b
Source dataset
uspto-grants-1983_05
Patent number
US04386220

Reaction notes

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