Phenol → 2H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester
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>C(Cl)Cl>[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 3
Product 1
Reagents, catalysts & solvents 1
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 flask equipped with a condenser, an internal thermometer and a mechanical stirrer. The solution was held under a static nitrogen atmosphere and stirred at about 65° C. for about 8 hrs. after which the THPE was isolated by precipitation with methylene chloride (4 mL/1 g of reaction mixture). The yield is given in Table III.
Workup
- customequipped with a condenser
Sources & evidence
- ORD record
- ord-0da812c26b7648a9ae2395fb97c3e439
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05969167
Reaction notes
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