Hydrochloric Acid → 4-Ethoxy-2,3-dihydroxybenzaldehyde

HRID 218260Notes

Reaction equation

HRID 218260 reaction equation
B(Cl)(Cl)Cl.C([O:7][C:8]1[C:15]([O:16]CC)=[C:14]([O:19][CH2:20][CH3:21])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11])C.C([O-])(O)=O.[Na+].Cl>C(Cl)Cl>[CH2:20]([O:19][C:14]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([OH:7])[C:15]=1[OH:16])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25135Boron Trichloride2×HCID 516892Sodium BicarbonateHCID 19956854Benzaldehyde, 2,3,4-triethoxy-

Product 1

HCID 448870214-Ethoxy-2,3-dihydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of boron trichloride (3.34 mL, 3.34 mmol 1M in DCM, 1 eq) was added dropwise to a solution of 33 (0.80 g, 3.34 mmol) in DCM at room temperature. The reaction mixture was stirred for 2 hours at this temperature then a further one equivalent of boron trichloride (3.34 mL, 3.34 mmol, 1M in DCM) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was cooled to 0° C. and saturated NaHCO3 aq. was added, then made acidic by the dropwise addition of conc. HCl. The reaction mixture was extracted with TBME (3×) and the organic phase was dried (Na2SO4) and concentrated in vacuo to give the crude product (1.4 g). Purification by column chromatography (SiO2 1:2 EtOAc:cyclohexane) gave 34 compound (0.46 g, 76%):

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionThe reaction mixture was extracted with TBME (3×)
  3. dry with materialthe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give the crude product (1.4 g)
  6. customPurification by column chromatography (SiO2 1:2 EtOAc:cyclohexane)

Sources & evidence

ORD record
ord-6a85e1181b5a4b4db397193c91dc10d0
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

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