Acetic Acid → HCID 66735236, compound

HRID 1641040Notes

Reaction equation

HRID 1641040 reaction equation
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:15](=[O:20])[CH2:14][CH2:13]2.C(O)(=O)C>C1(C)C=CC=CC=1.O>[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([C:3]([O:6][CH3:7])=[O:8])=[C:15]([OH:20])[CH2:14][CH2:13]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 44561396-Chloro-2-tetralone

Product 1

HCID 66735236HCID 66735236, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

10.1 g (252 mmol) of 60% sodium hydride in oil, 621 ml of toluene and 14.18 ml (163 mmol) of dimethyl carbonate are introduced into a 2 l reactor. The reaction mixture is stirred at reflux for 1 h. A solution of 15.2 g (84 mmol) of 6-chloro-3,4-dihydro-1H-naphthalen-2-one in 268 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 92 ml of acetic acid. 114 ml of water are added and the separated organic phase is separated by settling and washed with three times 150 ml of water and then with 100 ml of a saturated aqueous sodium chloride solution. The organic phase is subsequently dried over magnesium sulphate and then concentrated under reduced pressure. The residue is purified by chromatography on a silica column (elution being carried out with a mixture of cyclohexane and of dichloromethane) to result in 12.8 g (53.6 mmol) of the expected product used as is 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 three times 150 ml of water
  6. dry with materialThe organic phase is subsequently dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by chromatography on a silica column (
  9. washelution
  10. additionbeing carried out with a mixture of cyclohexane and of dichloromethane)

Sources & evidence

ORD record
ord-c032fd4eb2b042e79a84c9c202ea1398
Source dataset
uspto-grants-2012_02
Patent number
US08114899B2

Reaction notes

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