Acetic Acid → HCID 22218197, compound

HRID 1166650Notes

Reaction equation

HRID 1166650 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2([CH3:14])[CH3:13])=[CH:5][C:4]=1[CH3:15].C(O)(=[O:18])C>O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6](=[CH:5][C:4]=1[CH3:15])[C:7](=[O:18])[CH2:8][CH2:9][C:10]2([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 22218219HCID 22218219, compound2×

Product 1

HCID 22218197HCID 22218197, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-methoxy-1,1,6-trimethyl-1,2,3,4-tetrahydronaphthalene (Compound 29, 14.7 g, 72.1 mmol) and 30 mL of glacial acetic acid at 0° C. was added a cold solution of CrO3 (14.5 g, 144.2 mmol) in 30 mL of glacial acetic acid and 15 mL of water. The resulting dark solution was stirred at 0° C. for 1 h, then quenched with NaOH 2N, extracted with diethyl ether, washed with brine, dried over MgSO4, and filtered. The solvent was removed to give 11.3 g (72%) of the title compound as a dark brown solid. PNMR (300 MHz, CDCl3) δ 1.38 (s, 6H), 1.98 (t, 2H, J=7.5 Hz), 2.10 (s, 3H), 2.68 (t, 2H, J=7.5 Hz), 3.90 (s, 3H), 6.76 (s, 1H), 7.83 (d, 1H).

Workup

  1. customquenched with NaOH 2N
  2. extractionextracted with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-ed47bc1396bb417391711d130143c0d9
Source dataset
uspto-grants-2003_09
Patent number
US06613917B1

Reaction notes

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