Hydroquinone → 2-Phenoxy-3,4-dihydro-2H-pyran

HRID 248317Notes

Reaction equation

HRID 248317 reaction equation
[C:1]1([O:7][CH:8]=[CH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10]([CH:12]=[CH2:13])=[O:11].C1(C=CC(O)=CC=1)O>>[O:7]([CH:8]1[CH2:9][CH2:13][CH:12]=[CH:10][O:11]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 7847AcroleinHCID 69840Phenyl vinyl ether

Product 1

HCID 149546232-Phenoxy-3,4-dihydro-2H-pyran

Procedure

45 g (375 mmol) of phenylvinyl ether, 21 g (375 mmol) of acrolein and 0.66 g (6 mmol) of hydroquinone are reacted in a pressure reactor for 1 h at 185° C. After cooling, 2-phenoxy-3,4-dihydro-2H-pyran is isolated by distillation at 80° C./0.0267 kPa in a yield of 30.2 (172 mmol; 46%) as a clear liquid.

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-1bcbefd22b83480ea39370c5c032c0c6
Source dataset
uspto-grants-1993_05
Patent number
US05210003

Reaction notes

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