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Sodium Hydroxide → 1,2-Difluoro-4,5-dimethylbenzene

HRID 613806
Notes
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Reaction equation

HRID 613806 reaction equation
Cl[C:2]1([F:12])[CH2:7][C:6]([CH3:8])=[C:5]([CH3:9])[CH2:4][C:3]1(F)[F:10].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[F:10][C:3]1[CH:4]=[C:5]([CH3:9])[C:6]([CH3:8])=[CH:7][C:2]=1[F:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 195936835-Chloro-1,2-dimethyl-4,4,5-trifluorocyclohexene

Product 1

HCID 142277911,2-Difluoro-4,5-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 5-chloro-1,2-dimethyl-4,4,5-trifluorocyclohexene of 12.6 g prepared in Example 14 was added 1.0 g of benzyltriethylammonium chloride, and then the reaction mixture was heated to 80° C. followed by slowly adding 40 g of 50% aqueous sodium hydroxide solution for 30 min. The reaction mixture was stirred for additional 2 hours at 80° C., and then the resultant was purified by steam distillation followed by separating the aqueous layer. The organic layer was dried with calcium chloride, and then 7.3 g of the desired product was collected by fractional distillation at temperature 150° C. as a colorless liquid.

Workup

  1. distillationthe resultant was purified by steam distillation
  2. customby separating the aqueous layer
  3. dry with materialThe organic layer was dried with calcium chloride
  4. distillation7.3 g of the desired product was collected by fractional distillation at temperature 150° C. as a colorless liquid

Sources & evidence

ORD record
ord-d168ffdbc1464913baf518db1544ccdc
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06008407

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes