Hydrochloric Acid → 4-(4-Methoxybenzyl)benzyl alcohol

HRID 1706698

Reaktionsgleichung

Reaktionsgleichung von HRID 1706698
B.[CH3:2][O:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.Cl>O1CCCC1>[CH3:2][O:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 2579874-(4-Methoxybenzyl)benzoic acid

Produkt 1

HCID 2584334-(4-Methoxybenzyl)benzyl alcohol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 110 ml. (0.11 m) of 1 M boron hydride (BH3) in tetrahydrofuran was slowly added to a solution of 24.2 g. (0.10 m) of 4-(4-methoxybenzyl)benzoic acid in 110 ml. of tetrahydrofuran at 0° C. The addition was complete in 20 minutes and the reaction mixture was stirred at room temperature for one hour. The reaction mixture was carefully acidified with hydrochloric acid and the solvent removed. The residue was partitioned between water and ether, and the ether layer was washed with aqueous sodium hydroxide, dried over anhydrous magnesium sulfate and concentrated to give 22.2 g. of 4-(4-methoxybenzyl)benzyl alcohol, m.p. 68°-72° C. when recrystallized from cyclohexane.

Aufarbeitung

  1. customat 0° C
  2. additionThe addition
  3. customthe solvent removed
  4. customThe residue was partitioned between water and ether
  5. washthe ether layer was washed with aqueous sodium hydroxide
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give 22.2 g
  9. customof 4-(4-methoxybenzyl)benzyl alcohol, m.p. 68°-72° C. when recrystallized from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-a86f90d241374e3398550ad79d59c2b6
Quelldatensatz
uspto-grants-1980_06
Patentnummer
US04208425

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