Water → (2-Iodo-5-methylphenyl)methanol

HRID 1596635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1596635
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].B.C1COCC1.O>C1COCC1>[I:11][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=1[CH2:7][OH:8]

Komponenten

5

Edukt 3

HCID 962WaterHCID 1429412-Iodo-5-methylbenzoic acidHCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 44238586(2-Iodo-5-methylphenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Methyl-2-iodobenzoic acid (100 g, 0.38 mol) is dissolved in THF (350 ml) and cooled in an ice bath. Borane-THF complex (380 ml of 1M in THF, 0.38 mol) is added dropwise. After addition is complete, the reaction is warmed to room temperature and stirred for 14 hours. The mixture is transferred to a large erienmeyer flask, cooled in an ice bath, and carefully quenched with water (250 ml). Evaporation of the THF on a rotovap gives a white suspension which is treated with additional water (1 L) and then filtered and dried in a vacuum dessicator over P2O5 to give 2-iodo-5-methylbenzyl alcohol as a white solid, m.p. 82-85°.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. additionAfter addition
  3. customThe mixture is transferred to a large erienmeyer flask
  4. temperaturecooled in an ice bath
  5. customcarefully quenched with water (250 ml)
  6. customEvaporation of the THF on a rotovap
  7. customgives a white suspension which
  8. filtrationfiltered
  9. dry with materialdried in a vacuum dessicator over P2O5

Quellen und Nachweise

ORD-Eintrag
ord-dbb4c565dba143cfa4d95a64438d64f3
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06291523B1

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