Ethylene Glycol → HCID 11244560, compound

HRID 1739481Notes

Reaction equation

HRID 1739481 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:18](O)[CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:11]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]1[O:20][CH2:19][CH2:18][O:8]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 7330872-(Benzyloxy)-5-bromobenzaldehyde

Product 1

HCID 11244560HCID 11244560, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-bromo-2-benzyloxybenzaldehyde, prepared from commercial 5-bromosalicylicaldehyde by benzylation according to the method given in Reference example 22a), (25 g, 74.6 mmol) in toluene (250 ml) was treated with ethylene glycol (5 ml), and p-toluenesulfonic acid (0.24 g). The reaction was heated to reflux with azeotropic removal of water (Dean Stark trap). After 2.5 hrs, no further water was collected. The reaction was cooled to ambient temperature and washed with saturated aqueous NaHCO3, dried (MgSO4 and evaporated to give 2-(2-benzyloxy-5-bromophenyl)-1,3-dioxolane as a pale orange solid (26.8 g). This material was used without purification.

Workup

  1. temperatureThe reaction was heated
  2. customno further water was collected
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried (MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-cf98b0a4bb1c473cb3841baa1c9ab23f
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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