Chlorine → HCID 44140051, compound

HRID 1496834Notes

Reaction equation

HRID 1496834 reaction equation
[C:1]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[C:15]([OH:17])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18]Cl>ClC1C=CC=CC=1>[Cl:18][C:9]12[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[C:15](=[O:17])[O:16][C:1]2([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 2756601HCID 2756601, compound

Product 1

HCID 44140051HCID 44140051, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
59 °C

Procedure

23.2 g (0.1 mol) of 2-benzoyl-cyclohexanecarboxylic acid and 100 ml of chorobenzene are heated to 55° C. while stirring. Chlorine gas is then slowly introduced into the suspension over two hours while maintaining the temperature at 58-60° C. When no more starting material is detected by thin layer chromatography (TLC) analysis, the slightly yellowish solution is purged with nitrogen during one hour and subsequently cooled to room temperature. The solvent is then distilled off in vacuum to give a yellowish oil which according to TLC analysis consists of two main products. These products are isolated via preparative column chromatography on silica gel, using white spirit/ethyl acetate 1:4 as the eluant. The first fraction isolated is obtained as white solid with a melting point of 89-92° C. and is identified by 1H-NMR and elemental analysis as 3a-chloro-3-hydroxy-3-phenyl-hexahydro-isobenzofuran-1-one 9.3 g (35% yield). The second fraction is obtained as viscous yellowish oil, which is identified by 1H-NMR and elemental analysis as 3,3a-dichloro-3-phenyl-hexahydro-isobenzofuran-1-one (6.7 g, 25% yield)

Workup

  1. customthe slightly yellowish solution is purged with nitrogen during one hour
  2. temperaturesubsequently cooled to room temperature
  3. distillationThe solvent is then distilled off in vacuum
  4. customto give a yellowish oil which
  5. customThese products are isolated via preparative column chromatography on silica gel
  6. customThe first fraction isolated
  7. customis obtained as white solid with a melting point of 89-92° C.

Sources & evidence

ORD record
ord-dfa516899ab04f1c91bf0b20cf796bfa
Source dataset
uspto-grants-2015_12
Patent number
US09199934B2

Reaction notes

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