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

HRID 7331

反応式

HRID 7331 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)触媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c09bba65c034d81b66bbb9495a49de8
出典データセット
uspto-grants-2006_08
特許番号
US07087273B2

関連ノート

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