Hydrochloric Acid → (4-Bromo-3,5-dimethoxyphenyl)methanol

HRID 1454116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454116
[Cl-].[Ca+2].[Cl-].[Br:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][C:8]([C:9](OC)=[O:10])=[CH:7][C:6]=1[O:17][CH3:18].[BH4-].[Na+].Cl>C(O)C.O1CCCC1>[Br:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[O:17][CH3:18]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 117713Methyl 4-bromo-3,5-dimethoxybenzoateHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Produkt 1

HCID 11149289(4-Bromo-3,5-dimethoxyphenyl)methanolAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of calcium chloride (46.5 kg) in ethanol (336 L) were added tetrahydrofuran (672 L) and methyl 4-bromo-3,5-dimethoxybenzoate (96.0 kg) to obtain a suspension. To the suspension was added sodium borohydride (31.7 kg) by portions at room temperature, and the mixture was stirred for about 9 hours at temperature of room temperature to 45° C. The reaction mixture was added dropwise to aqueous HCl solution and stirred for about 16 hours at room temperature. Organic solvent was removed in vacuo, and water (1440 L) was added to the residue and stirred for 1 hour at 50° C. After cooling, the crystalline precipitates were collected by filtration and dried to yield 4-bromo-3,5-dimethoxybenzyl alcohol (83.3 kg) as colorless crystals.

Aufarbeitung

  1. customto obtain a suspension
  2. stirringstirred for about 16 hours at room temperature
  3. customOrganic solvent was removed in vacuo, and water (1440 L)
  4. additionwas added to the residue
  5. stirringstirred for 1 hour at 50° C
  6. temperatureAfter cooling
  7. customthe crystalline precipitates
  8. filtrationwere collected by filtration
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dd70d7dcf4774a7dbebf137adfd17021
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476758B2

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