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

HRID 7331

Reaction equation

HRID 7331 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[OH:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1.C(Cl)Cl>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CCOCC>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 111836454-(tetrahydro-2H-pyran-2-yloxy)benzoic acidYield 86.2%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 3283Diethyl EtherSolvent

Procedure

Into a 300 ml three neck flask were charged 25.4 g of 2,3-dihydropyran (reagent, manufactured by Tokyo Kasei Kogyo Co., Ltd.), 41.4 g of p-hydroxybenzoic acid (reagent, manufactured by Tokyo Kasei Kogyo Co., Ltd.), and 3.7 g of pyridinium p-toluenesulfonate (reagent, manufactured by Tokyo Kasei Kogyo Co., Ltd.). The mixture was dissolved after addition of 20 ml of methylene chloride and 80 ml of absolute ether. After the mixture was vigorously stirred for about 3 hours, it was extracted 3 times with 70 ml of a 10% sodium hydroxide aqueous solution. The resulting extracted solution was neutralized with 1 N of hydrochloric acid until the pH is made to 6. The resulting precipitate was filtered and dried in a vacuum thereby obtaining 57.4 g of crude p-tetrahydropyranyloxy benzoic acid.

Workup

  1. dissolutionThe mixture was dissolved
  2. extractionit was extracted 3 times with 70 ml of a 10% sodium hydroxide aqueous solution
  3. extractionThe resulting extracted solution
  4. filtrationThe resulting precipitate was filtered
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-1c09bba65c034d81b66bbb9495a49de8
Source dataset
uspto-grants-2006_08
Patent number
US07087273B2

Linked notes

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