Hydrochloric Acid → HCID 21524352, compound

HRID 917927Notes

Reaction equation

HRID 917927 reaction equation
[O:1]=[CH:2][C:3]([Cl:6])([Cl:5])[Cl:4].[C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].[Cl-].[Al+3].[Cl-].[Cl-].Cl>O>[C:7]([C:11]1[CH:16]=[CH:15][C:14]([CH:2]([OH:1])[C:3]([Cl:6])([Cl:5])[Cl:4])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6407ChloralHCID 7366Tert-Butylbenzene2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 21524352HCID 21524352, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 22 g (0.15 mole) of chloral and 15g of tert-butylbenzene was added in ten portions alternatively with 4.4g (0.03 mole) of aluminum chloride to a 120g portion of tert-butylbenzene with vigorous stirring at 5°C. The mixture was stirred at 20°C. for 0.5 hr. and again cooled to 5°C. before 40 ml of 6N HCl was added dropwise. The mixture was diluted with 20 ml of water and the organic products were extracted into ethyl ether (2 × 100 ml). The etheral solution was washed with 5% HCl, water, aqueous sodium carbonate and brine, dried over magnesium sulfate and concentrated. A 27g portion of the 33g residue was distilled via short path to provide 18.4g of a colorless, viscous product: Bp 144°C (0.2mm); ir (film) 2.85 (s), 3.4 (s), 9.4 (s), 12.1 (s), 12.8 (s) microns; nmr (CDCl3) 7.40 (4H, m), 5.06 (1H,s), 3.56 (1H, s), 1.28 (9H, s) ppm.

Workup

  1. stirringThe mixture was stirred at 20°C. for 0.5 hr
  2. additionwas added dropwise
  3. extractionthe organic products were extracted into ethyl ether (2 × 100 ml)
  4. washThe etheral solution was washed with 5% HCl, water, aqueous sodium carbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. distillationA 27g portion of the 33g residue was distilled via short path
  8. customto provide 18.4g of a colorless, viscous product

Sources & evidence

ORD record
ord-4d2903e42d59469ea99ed9b86d0b900d
Source dataset
uspto-grants-1976_07
Patent number
US03968168

Reaction notes

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