Hydrochloric Acid → 2,3-Dihydroxy-4-methoxybenzaldehyde

HRID 273198

Reaction equation

HRID 273198 reaction equation
C[O:2][C:3]1[C:10]([O:11]C)=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].B(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+].Cl>ClCCl>[OH:2][C:3]1[C:10]([OH:11])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25135Boron TrichlorideHCID 750062,3,4-TrimethoxybenzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 115573522,3-Dihydroxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3,4-trimethoxybenzaldehyde, 1 (9.8 g, 50 mmol) was dissolved in anhydrous dichloromethane (150 ml) under argon at ambient temperature. It was stirred for 10 minutes and boron trichloride (100 ml, 100 mmol, 2 eq; 1.0M solution in dichloromethane) was added. The dark reaction mixture was stirred for 24 hours and then slowly poured into 10% sodium bicarbonate (aq) (40 g/360 ml). The resulting solution was acidified with concentrated hydrochloric acid to pH 1. The dichloromethane layer was separated and the aqueous layer was extracted with ethyl acetate (4×100 ml) and dried. Evaporation of the solvent in vacuo gave a brown oil which was absorbed onto silica gel and subjected to flash chromatography (70:30, hexane-ethyl acetate). The diol 2 was obtained as a pale yellow solid (6.70 g, 80%).

Workup

  1. customThe dark reaction mixture
  2. stirringwas stirred for 24 hours
  3. customThe dichloromethane layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (4×100 ml)
  5. customdried
  6. customEvaporation of the solvent in vacuo
  7. customgave a brown oil which
  8. customwas absorbed onto silica gel

Sources & evidence

ORD record
ord-11fa3ec9cf4b4691a15ddb9f4e4f61ea
Source dataset
uspto-grants-2008_11
Patent number
US07456214B2

Linked notes

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