Hydrochloric Acid → HCID 21270011, compound

HRID 1194364Notes

Reaction equation

HRID 1194364 reaction equation
[Br:1][C:2]1[C:3]([OH:14])=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5](OC)=[O:6].[H-].[Al+3].[H-].[H-].Cl>O1CCCC1.O>[Br:1][C:2]1[C:3]([OH:14])=[C:4]([CH2:5][OH:6])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21269999HCID 21269999, compoundHCID 21584524Aluminiumhydride

Product 1

HCID 21270011HCID 21270011, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

28 g (0.12 mole) of methyl 3-bromo-2-hydroxy-4-methoxybenzoate (prepared according to the method of T. M. CRESP et al., J. Chem. Soc. Perkin Trans., Part 1, (1973), 340-345) dissolved in 250 ml of tetrahydrofuran, are added dropwise, in the course of 75 minutes, at 0° C. to a suspension of 6.06 g (0.159 mole) oflithium aluminum hydride in 100 ml of tetrahydrofuran. The reaction mixture is stirred for 3 hours at ambient temperature. Subsequently, there is added a mixture of 11.5 ml of water and 12 ml of tetrahydrofuran, followed by acifification with 28.6 ml of concentrated hydrochloric acid dissolved in 300 ml of water. The mixture is extracted with dichloromethane. The organic phases are washed with water, dried over anhydrous sodium sulfate and then evaporated pressure. The residue (22.9 g) is used as such in the following step. Yield: 91% of theory.

Workup

  1. additionSubsequently, there is added
  2. extractionThe mixture is extracted with dichloromethane
  3. washThe organic phases are washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated pressure

Sources & evidence

ORD record
ord-eb07475cd3d84699bdfadf42cecf8bc1
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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