Toluene → 3-Methoxycyclohex-2-en-1-one

HRID 1960180Notes

Reaction equation

HRID 1960180 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[C:9]1(C)C=CC=CC=1.C(OC)(OC)OC.O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:9][O:7][C:3]1[CH2:4][CH2:5][CH2:6][C:1](=[O:8])[CH:2]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 9005Trimethyl orthoformateHCID 104341,3-CyclohexanedioneHCID 86626551p-Toluenesulfonic acid dihydrate

Product 1

HCID 855973-Methoxycyclohex-2-en-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 21 three-necked flask, 100 g (0.89 mol) of cyclohexane-1,3-dione are initially charged and dissolved in 300 ml of methanol, 1000 ml of toluene and 97.6 ml of trimethyl orthoformate, 5 g of p-toluenesulphonic acid dihydrate are added and the mixture is heated under reflux for 2 h. After cooling, the mixture is washed 4× with in each case 200 ml of 10% strength NaOH and the organic phase is dried over sodium sulphate and concentrated on a rotary evaporator. This gives 73.4 g of a light-brown oil which is used for the next step without further purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. washthe mixture is washed 4× with in each case 200 ml of 10% strength NaOH
  5. dry with materialthe organic phase is dried over sodium sulphate
  6. concentrationconcentrated on a rotary evaporator
  7. customThis gives 73.4 g of a light-brown oil which is used for the next step without further purification

Sources & evidence

ORD record
ord-e00b58e7d36e4df0bd99b1aded0eabc3
Source dataset
uspto-grants-2013_04
Patent number
US08410289B2

Reaction notes

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