Ethylene Glycol → HCID 59773648, compound

HRID 2220577Notes

Reaction equation

HRID 2220577 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]3[CH2:16][CH2:15][CH:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[C:19]([F:26])[C:18]=4[F:27])[CH2:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.O.C(O)CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:24]([O:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]2[CH2:15][CH2:16][CH:11]([CH:8]3[CH2:9][CH2:10][C:5]4([O:1][CH2:2][CH2:3][O:4]4)[CH2:6][CH2:7]3)[CH2:12][CH:13]=2)=[C:18]([F:27])[C:19]=1[F:26])[CH3:25]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 69220745HCID 69220745, compound

Product 1

HCID 59773648HCID 59773648, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

250 g of crude 4-(1,4-dioxaspiro[4.5]dec-8-yl)-1-(4-ethoxy-2,3-difluorophenyl)cyclohexan in 1000 ml of toluene are heated on a water separator for 3 h together with 80.0 ml (1.43 mol) of ethylene glycol with addition of 12.0 g (0.06 mol) of p-toluenesulfonic acid monohydrate. After cooling, the batch is washed successively with water, sat. sodium hydrogencarbonate solution and sat. sodium chloride solution. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is crystallised from acetonitrile, giving 8-[4-(4-ethoxy-2,3-difluorophenyl)cyclohex-3-enyl]-1,4-dioxaspiro[4.5]decane as colourless solid.

Workup

  1. temperatureAfter cooling
  2. washthe batch is washed successively with water, sat. sodium hydrogencarbonate solution and sat. sodium chloride solution
  3. customThe solution is dried
  4. concentrationconcentrated to dryness
  5. customThe crude product is crystallised from acetonitrile

Sources & evidence

ORD record
ord-ae628201f57b4be2873b4a068167ed42
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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