Triethylamine → HCID 21540675, compound

HRID 1075738Notes

Reaction equation

HRID 1075738 reaction equation
[Cl:1][C:2]([Cl:15])([Cl:14])[CH2:3][C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:7])[CH2:5][OH:6].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([O:6][CH2:5][C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:7])[CH2:3][C:2]([Cl:14])([Cl:15])[Cl:1])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 21540699HCID 21540699, compound

Product 1

HCID 21540675HCID 21540675, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4,4,4-Trichloro-2-phenyl-2-hydroxybutanol (160 grams; 0.60 mole) was mixed with about 2000 milliliters (ml.) of methylene chloride and triethylamine (63.6 grams; 0.63 mole) was added thereto. The resulting mixture was cooled in an ice-methanol bath to a temperature of about -6 to about -8° C. Methanesulfonyl chloride (69 grams; 0.60 mole) in about 250 ml. of methylene chloride was added dropwise to the stirred reaction mixture over a period of about 45 minutes. The reaction mixture temperature was maintained below about 0° C. during the addition and, following the completion of the methanesulfonyl chloride solution; the reaction mixture temperature was allowed to come to room temperature. Thereafter, the reaction mixture was washed with water (four - 700 ml. portions), then with 700 ml. of a 10% sodium carbonate solution, and finally with another 700 ml. portion of water. An additional 600 ml. of methylene chloride was added to the organic product layer which was then dried over sodium sulfate. The volume of the organic product mixture was reduced to about 400 ml. by evaporation of the carrier medium in vacuo. The resulting white product precipitate was obtained by filtration. As a result of such operations, the desired 4,4,4-trichloro-2-phenyl-2-hydroxybutyl 1-methanesulfonate product was obtained as a white crystalline solid having a melting point of 128°-130° C.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was cooled in an ice-methanol bath to a temperature of about -6 to about -8° C
  3. temperatureThe reaction mixture temperature was maintained below about 0° C. during the addition
  4. customto come to room temperature
  5. washThereafter, the reaction mixture was washed with water (four - 700 ml. portions)
  6. additionof methylene chloride was added to the organic product layer which
  7. dry with materialwas then dried over sodium sulfate
  8. customby evaporation of the carrier medium in vacuo
  9. customThe resulting white product precipitate was obtained by filtration
  10. customAs a result of such operations

Sources & evidence

ORD record
ord-19625945888f4b39944b3105277fecbf
Source dataset
uspto-grants-1976_05
Patent number
US03954440

Reaction notes

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