Chloroform → HCID 15537314, compound

HRID 1248333Notes

Reaction equation

HRID 1248333 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)Cl.C[C:21](=[O:24])[CH2:22][CH3:23].C([N+]([CH2:37][CH3:38])(CC)CC)C1C=CC=CC=1.[OH-:39].[Na+].[H][H]>Cl>[C:11]([C:7]1[CH:8]=[C:9]([C:22]([CH3:23])([CH2:37][CH3:38])[C:21]([OH:24])=[O:39])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Participants

8

Reactant 6

HCID 6212ChloroformHCID 6569Methyl Ethyl KetoneHCID 14798Sodium HydroxideHCID 17208BenzyltriethylammoniumHCID 314052,6-Di-tert-butylphenolHCID 178418361HCID 178418361, compound

Product 1

HCID 15537314HCID 15537314, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

0.1 mole of 2,6-di-t-butylphenol, 0.12 mole of chloroform, 1 mole of 2-butanone, and 0.003 mole of benzyltriethylammonium were mixed in the 500 ml three-neck reactor while stirring. 0.5 mole of powdered sodium hydroxide was added in small portions during a 30 minute period. After the addition, the reaction temperature was slowly raised to 10° and stirred overnight. 200 ml of 4N HCl then was added slowly. The resulting 2 layers were separated. The aqueous layer was extracted twice with 50 ml methylene chloride and this was combined with the organic layer, then dried with sodium sulfate and concentrated. The residue was washed with hexanes to obtain crystals in 80% yield. The melting point was 141°-144° C.; molecular weight 306; carbon-calculated 74.47%, found 74.60%; hydrogen-calculated 9.87%, found 9.89%.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction temperature was slowly raised to 10°
  3. stirringstirred overnight
  4. customThe resulting 2 layers were separated
  5. extractionThe aqueous layer was extracted twice with 50 ml methylene chloride
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. washThe residue was washed with hexanes
  9. customto obtain crystals in 80% yield

Sources & evidence

ORD record
ord-79222fa492bc42b79a16f6c81ebba106
Source dataset
uspto-grants-1985_06
Patent number
US04523032

Reaction notes

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