Water → (+/-)-3,5-Dimethylphenyl alpha-chlorobenzeneacetate

HRID 991355Notes

Reaction equation

HRID 991355 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[C:8]([CH3:10])[CH:9]=1.[Cl:12][CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14](Cl)=[O:15].O>CN(C=O)C>[Cl:12][CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]([O:11][C:6]1[CH:7]=[C:8]([CH3:10])[CH:9]=[C:4]([CH3:3])[CH:5]=1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 79483,5-DimethylphenolHCID 24758Sodium hydrideHCID 102902Chloro(phenyl)acetyl chloride

Product 1

HCID 18630849(+/-)-3,5-Dimethylphenyl alpha-chlorobenzeneacetateYield 7.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (2 g) was added portionwise to a solution of 3,5-dimethylphenol (6.1 g) in DMF (50 ml). The mixture was stirred for 30 minutes and added dropwise at a temperature below 30° C. to a solution of 2-chloro-2-phenylacetylchloride (9.45 g) in DMF (50 ml). The mixture was stirred overnight, decomposed with water (5 ml) and the solvent was evaporated. Water was added and the mixture was extracted with DCM. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent: hexane/DIPE 100/0, 98/2 and 95/5). The pure fractions were collected and the solvent was evaporated [residue; yielding 10.82 g (79%)]. A small amount of the obtained residue was crystallized from DIPE, the precipitate was filtered off and the solvent was evaporated, yielding 1 g of (±)-3,5-dimethylphenyl α-chlorobenzeneacetate (intermediate 5; mp. 79.0° C.).

Workup

  1. stirringThe mixture was stirred overnight
  2. customthe solvent was evaporated
  3. additionWater was added
  4. extractionthe mixture was extracted with DCM
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified over silica gel on a glass
  9. filtrationfilter (eluent: hexane/DIPE 100/0, 98/2 and 95/5)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. custom[residue; yielding 10.82 g (79%)]
  13. customA small amount of the obtained residue was crystallized from DIPE
  14. filtrationthe precipitate was filtered off
  15. customthe solvent was evaporated

Sources & evidence

ORD record
ord-94a6083cd4224b159779b5fbdb708f33
Source dataset
uspto-grants-2002_10
Patent number
USRE037886E1

Reaction notes

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