Chloral → HCID 53739337, compound

HRID 1413230Notes

Reaction equation

HRID 1413230 reaction equation
[CH:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[O:9]=[CH:10][C:11]([Cl:14])([Cl:13])[Cl:12].[Cl-].[Al+3].[Cl-].[Cl-]>Cl>[CH:1]1([CH:10]([OH:9])[C:11]([Cl:14])([Cl:13])[Cl:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6407ChloralHCID 136091-CycloocteneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 53739337HCID 53739337, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of cyclooctene (28 g; 254 m. moles) and chloral (36 g; 244 m. moles) in light petroleum (b.p. 80°-100° C.; 200 ml) was stirred and cooled and aluminum chloride (4 g; 30 m. moles) was added. The reaction was allowed to proceed for a period of 1 hour and was then stirred at room temperature for a further 31/2 hours. Ice (150 g) and concentrated hydrochloric acid (50 ml) was added, the mixture extracted with light petroleum (b.p. 40°-60° C.; 2×400 ml) and the combined extracts washed with saturated aqueous sodium carbonate (2×100 ml) and water (100 ml). The dried (Na2SO4) extract was evaporated to give crude 1-(2-cycloocten-1-yl)-2,2,2-trichloroethanol (61.4 g) as a brown oil.

Workup

  1. temperaturecooled
  2. extractionthe mixture extracted with light petroleum (b.p. 40°-60° C.; 2×400 ml)
  3. washthe combined extracts washed with saturated aqueous sodium carbonate (2×100 ml) and water (100 ml)
  4. dry with materialThe dried (Na2SO4)
  5. extractionextract
  6. customwas evaporated

Sources & evidence

ORD record
ord-eae5e469eda741eea59fe8f63c6d1e0e
Source dataset
uspto-grants-1981_02
Patent number
US04249015

Reaction notes

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