4-Hydroxybenzoic Acid → 4-(tetrahydro-2H-pyran-2-yloxy)benzoic acid

HRID 424303

Reaction equation

HRID 424303 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:28]1[CH:33]=[CH:32][CH2:31][CH2:30][CH2:29]1>C(OCC)C>[O:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]1[O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 80803,4-dihydro-2H-pyranHCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 111836454-(tetrahydro-2H-pyran-2-yloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice-cooled mixture of 4-hydroxybenzoic acid (13.81 g) in 250 ml of diethylether containing 1.98 g of pyridinium p-toluenesulphonic acid, 3,4-dihydro-2H-pyran (16 g) was drop wise added. After complete addition stirring was continued at temperature below +8° C. for 4 h and the white precipitate was filtered off, washed twice with 100 ml of +4° C. pre-cooled diethylether and dried to give nearly pure 4-(tetrahydro-2H-pyran-2-yloxy)benzoic acid as white powder.

Workup

  1. additionwise added
  2. additionAfter complete addition
  3. filtrationthe white precipitate was filtered off
  4. washwashed twice with 100 ml of +4° C.
  5. temperaturepre-cooled diethylether
  6. customdried

Sources & evidence

ORD record
ord-c7763484ead34970ac2552da47af3675
Source dataset
uspto-grants-2012_01
Patent number
US08105662B2

Linked notes

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