3,4-dihydro-2H-pyran → Ethyl phenylacetate

HRID 1078698Notes

Reaction equation

HRID 1078698 reaction equation
O[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O-:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.O1C=CC[CH2:14][CH2:13]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:13]([O:11][C:9](=[O:10])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1)[CH3:14]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 6950813HCID 6950813, compound

Product 1

HCID 7590Ethyl phenylacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 116 g (0.644 mol) of the above 3hydroxyphenylacetate in 645 ml dichloromethane and 64.6 ml (0.71 mol) dihydropyran was added a few crystals of 4-toluenesulfonic acid monohydrate. The reaction was stirred for 3 hours at 0° and then added to 200 ml saturated sodium bicarbonate. The organic extract was dried over magnesium sulfate and evaporated to give 161 g (95%) of 3-(tetrahydro-2H-pyran-2-yl)oxy]-phenylacetic acid ethyl ester as an oil.

Workup

  1. extractionThe organic extract
  2. dry with materialwas dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-858463d869204d0e8362b609ce2ff436
Source dataset
uspto-grants-1996_08
Patent number
US05550152

Reaction notes

Loading…