Hydrochloric Acid → 3-Chloro-2-hydroxybenzaldehyde

HRID 1739492Notes

Reaction equation

HRID 1739492 reaction equation
[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].Cl>COCCOCCOC>[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 30225173-Chloro-2-hydroxybenzoyl chlorideHCID 16684435Lithium tritertbutoxyaluminohydride

Product 1

HCID 5196513-Chloro-2-hydroxybenzaldehydeYield 14.9%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
-70 °C

Procedure

3-Chloro-2-hydroxybenzoylchloride (8.7 mmol) was dissolved in diglyme (10 ml) and cooled to -70° C. under argon. Lithium tritertbutoxyaluminohydride (0.5M, 34.8 ml 17.4 mmol) was added via syringe keeping the temperature below -60° C. The reaction was stirred at -60° C. for 2% hours. The reaction mixture was poured onto ice, acidified with concentrated HCl and extracted with ethyl acetate (2×). The organic phases were combined, dried over MgSO4 and evaporated. Flash chromatography (eluant: CH2Cl2 /hexanes) gave the title product (0.2 g, 1.3 mmol). MS (CI+) (M+NH4)+ 174

Workup

  1. customthe temperature below -60° C
  2. additionThe reaction mixture was poured onto ice
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-fbc4e3a475b04882a81d9f2edec511a5
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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