对羟基苯甲酸 → 4-(tetrahydro-2H-pyran-2-yloxy)benzoic acid

HRID 7331笔记

反应方程式

HRID 7331 反应方程式
[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

参与物

6

反应物 3

HCID 135对羟基苯甲酸HCID 6344二氯甲烷HCID 80803,4-二氢-2H-吡喃

产物 1

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

试剂、催化剂与溶剂 2

HCID 4661024-甲基苯磺酸吡啶催化剂HCID 3283乙醚溶剂

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-1c09bba65c034d81b66bbb9495a49de8
来源数据集
uspto-grants-2006_08
专利号
US07087273B2

反应笔记

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