Hydrochloric Acid → HCID 69225494, compound

HRID 1027869Notes

Reaction equation

HRID 1027869 reaction equation
[H-].[Na+].[CH:3]1[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.[C:17](=O)([O:20]C)[O:18][CH3:19]>>[CH3:19][O:18][C:17]([CH:13]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=2[C:14]1=[O:15])=[O:20]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl Carbonate2×HCID 24758Sodium hydrideHCID 2763657,8,9,10-tetrahydrobenzo[8]annulen-5(6h)-one

Product 1

HCID 69225494HCID 69225494, compound

Conditions

Temperature
85 °C

Procedure

Dimethyl carbonate (20 mL) was treated with NaH (60% dispersed in oil, 660 mg, 46 mmol), heated at 85° C., treated dropwise with a solution of 7,8,9,10-tetrahydro-6H-benzocycloocten-5-one (prepared according to Richard W. Thies, J. Org. Chem. 42(2), 280-281, 1977) (950 mg, 5.5 mmol) in dimethyl carbonate (10 mL), stirred at 85-90° C. for three hours, cooled to 0° C., acidified by the slow addition of 1 M HCl (50 mL) and extracted with ether (150 mL). The organic was isolated, washed with brine, dried (MgSO4) and concentrated to provide the title compound.

Workup

  1. temperaturecooled to 0° C.
  2. extractionextracted with ether (150 mL)
  3. customThe organic was isolated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7742cbf9d5f54d43ad3ed13aa0022d09
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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