Water → HCID 19780713, compound

HRID 2081810Notes

Reaction equation

HRID 2081810 reaction equation
O[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH2:10][CH2:11][CH2:12][C:13]([CH3:16])([OH:15])[CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:14][C:13]1([CH3:16])[CH2:12][CH2:11][CH2:10][C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[O:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 19780704HCID 19780704, compound

Product 1

HCID 19780713HCID 19780713, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of the diol (D) (100 mg, 0.45 mM) and p-toluenesulphonic acid (10 mg) in benzene (20 ml) was heated for 1 hour under reflux in an apparatus for the azeotropic removal of water. The reaction solution was cooled, and washed with aqueous sodium hydroxide (2M), followed by brine. The dried (Na2SO4) solution was concentrated in vacuo. The residual oil was purified by flash chromatography, eluting with toluene/hexane (1:1 v/v), to give 2,3,4,5-tetrahydro-2,2,6,8-tetramethyl-1-benzoxepin (E) as a colourless oil (90 mg, 98% yield); NMR: 1.25(6H,s), 1.63(4H,m), 2.23(3H,s), 2.25(3H,s), 2.73(2H,m), 6.57(1H,s), 6.69(1H,s).

Workup

  1. temperatureThe reaction solution was cooled
  2. washwashed with aqueous sodium hydroxide (2M)
  3. dry with materialThe dried (Na2SO4) solution
  4. concentrationwas concentrated in vacuo
  5. customThe residual oil was purified by flash chromatography
  6. washeluting with toluene/hexane (1:1 v/v)

Sources & evidence

ORD record
ord-091b704426454f99aac677dd87c7e378
Source dataset
uspto-grants-1993_02
Patent number
US05185452

Reaction notes

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