Acetic Acid → HCID 66735659, compound

HRID 1641041Notes

Reaction equation

HRID 1641041 reaction equation
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][C:17](=O)[CH2:18]2)=[CH:13][CH:12]=1.C(O)(=[O:24])C>C1(C)C=CC=CC=1.CCCCCCC.C(Cl)Cl.O>[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14](=[CH:13][CH:12]=1)[C:15]([C:3]([O:6][CH3:7])=[O:8])=[C:16]([OH:24])[CH2:17][CH2:18]2

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 777857-Methoxy-2-tetralone

Product 1

HCID 66735659HCID 66735659, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

3.4 g (85.12 mmol) of 60% sodium hydride in oil, 180 ml of toluene and 4.78 ml (56.75 mmol) of dimethyl carbonate are introduced into a 1 l reactor. The reaction mixture is stirred at reflux for 1 h. A solution of 5 g (28.37 mmol) of 7-methoxy-3,4-dihydro-1H-naphthalen-2-one in 100 ml of toluene is subsequently added. The reaction mixture is heated at reflux for 24 h. The reaction mixture is subsequently cooled to 0° C. and then acidified by addition of 30 ml of acetic acid. 30 ml of water are added and the separated organic phase is separated by settling and washed with two times 50 ml of water and then with 50 ml of a saturated aqueous sodium chloride solution. The organic phase is subsequently dried over magnesium sulphate and then concentrated under reduced pressure. After purification by chromatography on a silica column (eluent: mixture of methylene chloride and of heptane), 3.9 g (16.64 mmol) of the expected product are obtained and are used as in the following stage.

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 24 h
  4. customthe separated organic phase is separated
  5. washwashed with two times 50 ml of water
  6. dry with materialThe organic phase is subsequently dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customAfter purification by chromatography

Sources & evidence

ORD record
ord-2ba041b0653b4f21a2bb66fc47377006
Source dataset
uspto-grants-2012_02
Patent number
US08114899B2

Reaction notes

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