Water → HCID 11535852, compound

HRID 1488721Notes

Reaction equation

HRID 1488721 reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.O=[C:26]1[CH2:30][CH2:29][CH:28]([C:31]([O:33]C)=[O:32])[CH2:27]1.O>C1(C)C=CC=CC=1>[C:31]([CH:28]1[CH2:29][CH2:30][C:26]2([O:6][CH2:5][C:2]([CH3:7])([CH3:1])[CH2:3][O:4]2)[CH2:27]1)([OH:33])=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 31344Neopentyl glycolHCID 2376403-Oxo-cyclopentanecarboxylic acid methyl esterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 11535852HCID 11535852, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

72.8 g (0.70 mole) of 2,2-dimethylpropane-1,3-diol and 12.2 g (0.05 mole) of pyridinium-4-toluenesulphonate are added one after another to 40.0 g (0.28 mole) of methyl 3-oxocyclopentane carboxylate OCCME in 560 ml of absolute toluene. The mixture is boiled for 1.5 hours in a water separator; after 30 minutes the solid is dissolved. Approximately 8 ml of H2O in total are separated out. After cooling, the solution is washed three times using 100 ml of H2O each time, the toluene phase is dried over MgSO4 and evaporated in vacuo. The oily residue is fractionally distilled in vacuo at 0.6 mbar over a metallised pin tube column 20 cm long.

Workup

  1. dissolutionafter 30 minutes the solid is dissolved
  2. customApproximately 8 ml of H2O in total are separated out
  3. temperatureAfter cooling
  4. washthe solution is washed three times
  5. dry with materialthe toluene phase is dried over MgSO4
  6. customevaporated in vacuo
  7. distillationThe oily residue is fractionally distilled in vacuo at 0.6 mbar over a metallised pin tube column 20 cm long

Sources & evidence

ORD record
ord-4c3753e109214f2e80c29f63c82bcbc5
Source dataset
uspto-grants-1997_10
Patent number
US05675005

Reaction notes

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