Acetic Acid → HCID 66680431, compound

HRID 1626749Notes

Reaction equation

HRID 1626749 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[Br-].[Na+].CC1[CH:13]=[CH:12][C:11]([C:14]([C:16]23[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]4)[CH2:17]2)[CH2:23]3)=[O:15])=[CH:10][CH:9]=1>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.O.O.O.O.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.O>[C:16]12([C:14]([C:11]3[CH:12]=[CH:13][C:2]([C:1]([OH:4])=[O:3])=[CH:9][CH:10]=3)=[O:15])[CH2:23][CH:22]3[CH2:21][CH:20]([CH2:19][CH:18]([CH2:24]3)[CH2:17]1)[CH2:25]2

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 253881Sodium BromideHCID 12189424HCID 12189424, compound

Product 1

HCID 66680431HCID 66680431, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 93021Manganese acetate tetrahydrateCatalystHCID 962WaterSolvent2×

Procedure

64.6 mL of acetic acid, 3.4 mL of water, 333 mg (1.34 mmol) of cobalt acetate tetrahydrate, 33 mg (0.134 mmol) of manganese acetate tetrahydrate and 138 mg (1.34 mmol) of sodium bromide were added to 3.4 g (13.4 mmol) of (4-methylphenyl) (adamantan-1-yl)methanone, and the mixture was stirred at room temperature for a short time. While blowing air into the mixture, the mixture was stirred in an oil bath at 100 to 110° C. for one day. The reaction mixture was cooled to room temperature, and water was added thereto. The precipitated solids were collected by filtration, washed with water, and air-dried, thereby giving 2.99 mg of 4-(adamantan-1-ylcarbonyl)benzoic acid (yield: 78%).

Workup

  1. stirringthe mixture was stirred in an oil bath at 100 to 110° C. for one day
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationThe precipitated solids were collected by filtration
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-feb3e1357e4b4a1b868b97cbc5d69f7a
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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