p-Toluenesulfonic acid → 3-[(2-Fluorophenyl)methoxy]oxolane

HRID 614695Notes

Reaction equation

HRID 614695 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:12][C:13]1[CH:26]=[CH:25][CH:24]=[CH:23][C:14]=1[CH2:15][O:16][CH:17]([CH2:20][CH2:21][OH:22])[CH2:18]O>O>[F:12][C:13]1[CH:26]=[CH:25][CH:24]=[CH:23][C:14]=1[CH2:15][O:16][CH:17]1[CH2:20][CH2:21][O:22][CH2:18]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 213266282-(2-Fluorobenzyloxy)-butane-1,4-diol

Product 1

HCID 213266183-[(2-Fluorophenyl)methoxy]oxolane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

0.1 g of p-toluenesulphonic acid was added to 4.26 g (0.02 mol) of 2-(2-fluorobenzyloxy)-butane-1,4-diol and the mixture was slowly heated to 200° C. under a waterpump vacuum. A mixture of water of reaction and 3-(2-fluorobenzyloxy)-tetrahydrofurane was obtained in the distillate. After fractional distillation, 3.8 g (97.5% of theory) of 3-(2-fluorobenzyloxy)-tetrahydrofurane of boiling point 140° C./14 mm Hg were obtained.

Sources & evidence

ORD record
ord-a56ddf4acd7b468da4f4fa74b0333203
Source dataset
uspto-grants-1979_03
Patent number
US04146384

Reaction notes

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