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

HRID 1454116Notes

Reaction equation

HRID 1454116 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 11149289(4-Bromo-3,5-dimethoxyphenyl)methanolYield 96.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dd70d7dcf4774a7dbebf137adfd17021
Source dataset
uspto-grants-2009_01
Patent number
US07476758B2

Reaction notes

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