Hydrochloric Acid → HCID 21269995, compound

HRID 1194366Notes

Reaction equation

HRID 1194366 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[BH4-].[Na+].O.Cl>O1CCCC1>[Br:1][C:2]1[C:3]([OH:13])=[C:4]([CH:10]([CH3:11])[OH:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 4311764Sodium borohydrideHCID 212700041-(3-Bromo-2-hydroxy-4-methoxyphenyl)ethanone

Product 1

HCID 21269995HCID 21269995, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

64.3 g (0.262 mole) of 3'-bromo-2'-hydroxy-4'-methoxyacetophenone (prepared according to the method of T. M. CRESP et al., J. Chem. Soc. Perkin Trans., Part 1, (1973), 340-345) dissolved in 560 ml of tetrahydrofuran, are added dropwise in the course of 80 minutes and at a temperature of from 13° to 18° C. to a suspension of 13.89 g (0.367 mole) of sodium borohydride in 300 ml of tetrahydrofuran. Thereafter, stirring is continued for 2 hours at ambient temperature. The reaction mixture is decomposed by the addition of 140 ml of tetrahydrofuran containing 3 ml of water, then 60 ml of water are added again thereto. The mixture is acidified by the addition of 415 ml of a 1N aqueous solution of hydrochloric acid. The tetrahydrofuran is removed under reduced pressure and the aqueous phase is extracted 4 times with dichloromethane. The organic phases are dried over anhydrous sodium sulfate and then distilled. The residue obtained(70 g) is used as such in the following step.

Workup

  1. customThe tetrahydrofuran is removed under reduced pressure
  2. extractionthe aqueous phase is extracted 4 times with dichloromethane
  3. dry with materialThe organic phases are dried over anhydrous sodium sulfate
  4. distillationdistilled
  5. customThe residue obtained(70 g)

Sources & evidence

ORD record
ord-7a3bdfecc47b45abb0aac0a01e75167f
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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