Sulfuric Acid → HCID 11291348, compound

HRID 1383947Notes

Reaction equation

HRID 1383947 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([OH:14])[C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Br:17][CH2:18][CH2:19]O.S(=O)(=O)(O)O>C1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[O:14][CH2:19][CH2:18][Br:17])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 70334,4'-DichlorobenzhydrolHCID 108982-Bromoethanol

Product 1

HCID 11291348HCID 11291348, compoundYield 8,380.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4,4′-dichlorobenzhydrol (4.40 g, 0.17 mmol) and 2-bromoethanol (3.0 g, 24.0 mmol) in benzene (50 ml) was treated with sulfuric acid (0.25 ml) and the resulting mixture was heated under reflux for 1 h. The cooled mixture was diluted with ethyl acetate (200 ml), washed with saturated sodium bicarbonate, brine and dried over magnesium sulfate. Evaporation of the solvent gave an oil which was chromatographed on silica gel using a mixture of toluene and hexane (1:1) as eluent to give the title compound as a clear oil (5.13 g, 82%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 h
  3. washwashed with saturated sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave an oil which
  7. customwas chromatographed on silica gel using
  8. additiona mixture of toluene and hexane (1:1) as eluent

Sources & evidence

ORD record
ord-d5d8e00d01ca44a6a48d91ddcfb9527b
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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