Water → 5-Hydroxy-5,6-dimethyl-dibenzo[a,e]cyclooct-11-ene

HRID 1651067Notes

Reaction equation

HRID 1651067 reaction equation
[CH3:1][CH:2]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[CH:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[C:3]1=[O:18].[CH3:19][Li].O>C(OCC)C>[OH:18][C:3]1([CH3:19])[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[CH:6]=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:2]1[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 67794300HCID 67794300, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 677948865-Hydroxy-5,6-dimethyl-dibenzo[a,e]cyclooct-11-ene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 5-methyl-6-oxo-dibenzo[a,e]cyclooctene (0.1 g) in anhydrous diethyl ether (10 ml) under nitrogen at 0° C. was added methyl lithium (0.43 ml of a 1.4 M solution in diethyl ether). After stirring for approximately 30 minutes water (10 ml) was added. The phases were separated and the ethereal layer was washed with water (2×10 ml), dried (Na2SO4) and the solvent removed in vacuo to give the title compound as a colourless solid (0.104 g), mP 86°-87° C. δ1.43 (CDCl3 360 MHz,) (3H, s, C--CH3), 1.44 (3H, d, J=7.0 Hz, --CH--CH3), 2.03 (1H, s, --OH), 4.07 (1H, q, J=7.0 Hz, --CH--CH3), 6.75 (1H, d, J=11.8 Hz, CHA =CHB), 6.96-7.21 (8H, m, ArH and CHA =CHB), 7.41 (1H, d J=7.5 Hz, ArH), 7.85 (1H, d J=7.9 Hz, ArH) m/e 250 (M+).

Workup

  1. additionwas added
  2. customThe phases were separated
  3. washthe ethereal layer was washed with water (2×10 ml)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-34edb77493e94b6c896999e0a751df64
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

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