Hydrochloric Acid → 2'-Fluoro-2-hydroxy-4-methoxy-3-methylbenzophenone

HRID 652883Notes

Reaction equation

HRID 652883 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH3:11].[F:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].[Al+3].[Cl-].[Cl-].[Cl-].Cl>ClC(Cl)C>[F:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](=[O:16])[C:8]1[CH:7]=[CH:6][C:5]([O:9][CH3:10])=[C:4]([CH3:11])[C:3]=1[OH:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 98082-Fluorobenzoyl chlorideHCID 797552,6-DimethoxytolueneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 130157162'-Fluoro-2-hydroxy-4-methoxy-3-methylbenzophenone

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
5 °C

Procedure

2,6-dimethoxytoluene (20.0 g) and o-fluorobenzoyl chloride (19.8 g) are dissolved in 250 ml of dichloroethane and chilled to 5° C. AlCl3 is added portionwise and when the addition is complete the reaction mixture is allowed to warm to room temperature over 30 minutes, then refluxed 30 minutes. It is then poured into 5% HCl and allowed to stand undisturbed 18 hours. Extraction with ether, followed by drying and concentration, gives crystalline material that is washed with hexane to give 2'-fluoro-2-hydroxy-4-methoxy-3-methylbenzophenone, mp 118°-120° C.

Workup

  1. additionwhen the addition
  2. temperatureto warm to room temperature over 30 minutes
  3. temperaturerefluxed 30 minutes
  4. extractionExtraction with ether
  5. customby drying
  6. concentrationconcentration
  7. customgives crystalline material that
  8. washis washed with hexane

Sources & evidence

ORD record
ord-616b0cf3c4e14731bcc43847f13f9a04
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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