Ethylene Glycol → 4-Bromo-3-(1,3-dioxolan-2-yl)phenol

HRID 1664336Notes

Reaction equation

HRID 1664336 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](O)[CH2:12][OH:13].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]1[O:13][CH2:12][CH2:11][O:5]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 3871792-Bromo-5-hydroxybenzaldehyde

Product 1

HCID 579687074-Bromo-3-(1,3-dioxolan-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-bromo-5-hydroxy-benzaldehyde compound 1 (15.0 g, 74.62 mmol) in toluene (100 mL) was added ethylene glycol (12.5 mL, 223.86 mmol) and p-TSA (1.42 g, 7.46 mmol). The solvent was removed under reduced pressure to give crude product 2 (20.0 g crude), which was used in the next step without further purification. 1H NMR 400 MHz (CDCl3) δ: 7.38 (d, J=8.6 Hz, 1H), 7.01 (d, J=2.7 Hz, 1H), 6.62 (d, J=8.2, 2.3 Hz, 1H), 6.01 (s, 1H), 4.20-4.01 (m, 4H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1f8a7be36e5143b29fb60076371636ea
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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