1-(cyclopent-1-en-1-yl)-3-methoxybenzene → HCID 20499284, compound

HRID 1578155Notes

Reaction equation

HRID 1578155 reaction equation
O.O.O.C([O-])(=[O:6])C.[Na+].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:17]2[CH2:21][CH2:20][CH2:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1>C(OO)(=O)C.ClCCl>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:17]23[O:6][CH:21]2[CH2:20][CH2:19][CH2:18]3)[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 2724811-(cyclopent-1-en-1-yl)-3-methoxybenzeneHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 20499284HCID 20499284, compoundYield 298%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6585Peracetic AcidSolvent

Procedure

A solution of sodium acetate trihydrate (6 g) in peracetic acid (38 ml) was added dropwise to a stirred solution of 1-(3-methoxyphenyl) cyclopentene (33.5 g) in dichloromethane (200 ml), maintaining the temperature in the range 0°-10°. The solution was stirred for 3 hours at room temperature and then washed with 8% aqueous sodium bicarbonate (700 ml) and 8% sodium thiosulphate solution (400 ml). The organic phase was separated, dried and evaporated and the residue was distilled in vacuo to give the title compound as a colourless oil (25 g) b.p. 89°-92° (0.01 mm).

Workup

  1. temperaturemaintaining the temperature in the range 0°-10°
  2. washwashed with 8% aqueous sodium bicarbonate (700 ml) and 8% sodium thiosulphate solution (400 ml)
  3. customThe organic phase was separated
  4. customdried
  5. customevaporated
  6. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-0f2e9478bf6445c1baf6d0eec77f9d60
Source dataset
uspto-grants-1981_09
Patent number
US04291059

Reaction notes

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