Acetic Anhydride → HCID 67547382, compound

HRID 2089496Notes

Reaction equation

HRID 2089496 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9]([CH3:15])([CH3:14])[CH:10]2[OH:13])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:23](OC(=O)C)(=[O:25])[CH3:24]>CN(C1C=CN=CC=1)C.ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9]([CH3:15])([CH3:14])[CH:10]2[O:13][C:23](=[O:25])[CH3:24])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 13124210HCID 13124210, compound

Product 1

HCID 67547382HCID 67547382, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphthalen-1-ol (1.40 g, 6.52 mmol) and DMAP (0.16 g, 1.30 mmol) in dichloromethane (30 mL) is added triethylamine (1.99 g, 19.55 mmol) and acetic anhydride (1.68 g, 16.29 mmol). After 45 min, the mixture is diluted with ethyl acetate and washed successively with 1M aqueous sodium bisulfate, saturated aqueous sodium bicarbonate, and brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated to give acetic acid 7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl ester, which is used in the next step without further purification.

Workup

  1. washwashed successively with 1M aqueous sodium bisulfate, saturated aqueous sodium bicarbonate, and brine
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fab86800d0224cd1805c35c4bf544b46
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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