Carbon Tetrachloride → 2-Chloro-4-(oxan-4-yl)phenol

HRID 1678972ノート

反応式

HRID 1678972 の反応式
S(Cl)(Cl)(=O)=O.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1.C(Cl)(Cl)(Cl)[Cl:20]>[OH-].[Na+]>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[CH:9][C:8]=1[Cl:20]

参加物

5

反応物 3

HCID 5943Carbon TetrachlorideHCID 24648Sulfuryl chlorideHCID 227373584-(Oxan-4-yl)phenol

生成物 1

HCID 184146372-Chloro-4-(oxan-4-yl)phenol

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

10 ml of sulfuryl chloride were added with stirring to a mixture of 14.1 g of 4-(p-hydroxyphenyl)-tetrahydropyran and 40 ml of carbon tetrachloride and the mixture was heated to 45°-50° C for 16 hours. The mixture was concentrated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with methylene chloride yielded a crystal product which was dissolved in 200 ml of N sodium hydroxide and the solution was washed with ether and acidified with 2N hydrochloric acid. The mixture was extracted with ether and the organic phase was washed with water, then an aqueous sodium bisulfite solution and then with water. The extracts were dried and evaporated to dryness to obtain 6.4 g of 4-(4-hydroxy-3-chlorophenyl)-tetrahydropyran melting at 123°-125° C.

後処理

  1. temperaturethe mixture was heated to 45°-50° C for 16 hours
  2. concentrationThe mixture was concentrated to dryness under reduced pressure
  3. customthe residue was chromatographed over silica gel
  4. washElution with methylene chloride
  5. customyielded a crystal product which
  6. washthe solution was washed with ether
  7. extractionThe mixture was extracted with ether
  8. washthe organic phase was washed with water
  9. customThe extracts were dried
  10. customevaporated to dryness

出典と根拠

ORDレコード
ord-3b17c930ff88481e8fd7784b76902d4a
出典データセット
uspto-grants-1978_03
特許番号
US04078076

反応ノート

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