Hydrochloric Acid → 6-Methyl-2-(trifluoroacetyl)tetralone

HRID 1941702

Reaction equation

HRID 1941702 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[CH3:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[CH2:19][CH2:18][CH2:17]2.Cl>CCOCC>[CH3:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[CH:19]([C:3](=[O:5])[C:2]([F:1])([F:8])[F:9])[CH2:18][CH2:17]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 1626203,4-dihydro-6-methylnaphthalen-1(2H)-oneHCID 10942334Sodium Methoxide

Product 1

HCID 223155526-Methyl-2-(trifluoroacetyl)tetraloneYield 85.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl trifluoroacetate (5.33 g, 37.5 mmol) was dissolved in ether (50 mL) and treated with a sodium methoxide solution (25% in methanol, 9.92 g, 45.9 mmol) followed by 6-methyltetralone (5.94 g, 37.1 mmol). The reaction was stirred at room temperature for 6.1 hours then treated with 1N HCl (20 mL). The organic layer was collected, washed with brine, dried over MgSO4, and concentrated in vacuo to give a brown oil (8.09 g) that was used in the next step without further purification.

Workup

  1. customThe organic layer was collected
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86e9ef1581f54ccbaf93858808191b56
Source dataset
uspto-grants-2013_03
Patent number
USRE044048E1

Linked notes

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