Phenol → 2H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

HRID 1292549Notes

Reaction equation

HRID 1292549 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3]C=1.SCC[C:11]([OH:13])=[O:12].[CH3:14]C1C=CC2C(=CC=C(C)C=2)C=1.CC(C1C=CC(O)=CC=1)=O>>[CH3:14][O:13][C:11]([CH:5]1[CH2:4][CH2:3][O:7][CH2:1][CH2:6]1)=[O:12]

Participants

5

Reactant 4

HCID 996PhenolHCID 65143-Mercaptopropionic AcidHCID 74694'-HydroxyacetophenoneHCID 113872,6-Dimethylnaphthalene

Product 1

HCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

Conditions

Temperature
65 °C

Procedure

A mixture of 94 grams (1.0 mol) of phenol, 5.31 g (0.0500 mol) of 3-mercaptopropionic acid, 10 g of LEWATIT BE ion exchange resin and 1.0 g of 2,6-dimethylnaphthalene (internal standard for liquid chromatography analysis) was heated to about 65° C. in a round bottom flack equipped with a distillation setup, an internal thermometer and a mechanical stirrer. The solution was continuously sparged with nitrogen (using a dip tube) to remove the water. To this mixture was added 11.35 g (0.8336 mol) of 4-hydroxyacetophenone. The mixture was stirred at about 65° C with the nitrogen sparge for about 8 hrs. The THPE was isolated by precipitation with methylene chloride (4 mL/1 g of reaction mixture) and the yield is given in Table III.

Workup

  1. customequipped with a distillation setup
  2. customThe solution was continuously sparged with nitrogen (using a dip tube)
  3. customto remove the water
  4. customsparge for about 8 hrs

Sources & evidence

ORD record
ord-2ac373a1a2fe408096c601926017e365
Source dataset
uspto-grants-1998_05
Patent number
US05756781

Reaction notes

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