Ethylene Glycol → HCID 58991877, compound

HRID 2220563Notes

Reaction equation

HRID 2220563 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:19][CH2:18][C:13]3([O:17][CH2:16][CH2:15][O:14]3)[CH2:12][CH:11]2O)=[C:6]([F:21])[C:5]=1[F:22])[CH3:2].O.C(O)CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:19][CH2:18][C:13]3([O:14][CH2:15][CH2:16][O:17]3)[CH2:12][CH:11]=2)=[C:6]([F:21])[C:5]=1[F:22])[CH3:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 58991866HCID 58991866, compound

Product 1

HCID 58991877HCID 58991877, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

609 g (about 1.94 mol) of crude 8-(4-ethoxy-2,3-difluorophenyl)-1,4-dioxaspiro[4.5]decan-7-ol in 2000 ml of toluene are heated on a water separator for 2 h together with 220 ml (3.93 mol) of ethylene glycol with addition of 36.1 g (0.19 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 (507 g of orange oil) is crystallised from ethanol at −20° C., giving 8-(4-ethoxy-2,3-difluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene as yellow 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 (507 g of orange oil) is crystallised from ethanol at −20° C.

Sources & evidence

ORD record
ord-b800cbee8efd41a794047059bf9643fe
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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