Sulfuric Acid → (3-Iodo-2-methylphenyl)methanol

HRID 1065557노트

반응식

HRID 1065557 반응식
Cl.[OH:2][CH2:3][C:4]1[C:5]([CH3:11])=[C:6]([CH:8]=[CH:9][CH:10]=1)N.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:21].[K+]>O.[Cu]>[I:21][C:6]1[C:5]([CH3:11])=[C:4]([CH:10]=[CH:9][CH:8]=1)[CH2:3][OH:2]

참가 물질

7

반응물 4

HCID 1118Sulfuric Acid2회HCID 4875Potassium IodideHCID 20270659(3-Amino-2-methylphenyl)methanol hydrochlorideHCID 23668193Sodium Nitrite

생성물 1

HCID 15035506(3-Iodo-2-methylphenyl)methanol수율 24.5%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 962Water용매3회

실험 절차

A stirred solution of 3-hydroxymethyl-2-methylaniline hydrochloride (43.4 g, 0.25 mole) and 17.2 ml of concentrated sulfuric acid in ice-water was cooled to 0°, and a solution of sodium nitrite (17.3 g, 0.25 mole) in water was added dropwise. Upon complete addition, the reaction mixture was stirred for an additional 0.5 hour, then an additional 8 ml of concentrated sulfuric acid was added dropwise. With the temperature maintained at 0°, a solution of potassium iodide (49.8 g, 0.30 mole) in water was added dropwise to the reaction mixture, followed by the addition of 0.1 gram of copper powder. The reaction mixture was slowly warmed to 70° where it stirred for 1 hour. The reaction mixture was then allowed to stand for 18 hours while cooling to room temperature. The reaction mixture was then taken up in water and extracted with chloroform. The chloroform extract was washed with an aqueous saturated solution of sodium bisulfite, then with water. The chloroform layer was dried and filtered. The filtrate was evaporated under reduced pressure to give 3-iodo-2-methylbenzyl alcohol (15.2 g) as a dark solid.

후처리

  1. additionUpon complete addition
  2. temperatureWith the temperature maintained at 0°
  3. temperatureThe reaction mixture was slowly warmed to 70° where it
  4. stirringstirred for 1 hour
  5. waitto stand for 18 hours
  6. extractionextracted with chloroform
  7. extractionThe chloroform extract
  8. washwas washed with an aqueous saturated solution of sodium bisulfite
  9. dry with materialThe chloroform layer was dried
  10. filtrationfiltered
  11. customThe filtrate was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-2de92ff7207b404abd0ed05b07f800d7
출처 데이터셋
uspto-grants-1982_05
특허 번호
US04329518

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