Ethylene Glycol → [2-(4-Fluorophenyl)-[1,3]dioxolan-2-yl]methanol

HRID 548193Notes

Reaction equation

HRID 548193 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.[CH2:12](O)[CH2:13][OH:14]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:9][OH:10])[O:14][CH2:13][CH2:12][O:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 28107151-(4-Fluorophenyl)-2-hydroxyethanone

Product 1

HCID 55253378[2-(4-Fluorophenyl)-[1,3]dioxolan-2-yl]methanolYield 72%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

The same reaction as in the synthesis of 3a was conducted from 1-(4-fluorophenyl)-2-hydroxyethanone (23.89 g, 155 mmol), ethylene glycol (42 mL, 780 mmol), p-toluenesulfonic acid monohydrate (0.5 g) and benzene (300 mL) and the resulting crude product was purified by a silica gel column chromatography (toluene:ethyl acetate=4:1) to give [2-(4-fluorophenyl)-[1,3]dioxolan-2-yl]methanol (22.05 g, 72%) as an oily product. 1H-NMR (DMSO-d6) δ: 3.51 (d, J=6.3 Hz, 2H), 3.75-3.81 (m, 2H), 3.99-4.07 (m, 2H), 4.94 (t, J=6.3 Hz, 1H), 7.13-7.19 (m, 2H), 7.42-7.47 (m, 2H).

Workup

  1. customThe same reaction
  2. customthe resulting crude product was purified by a silica gel column chromatography (toluene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-4c40307b0d0c4652b0d82449776fda23
Source dataset
uspto-grants-2011_05
Patent number
US07939552B2

Reaction notes

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