Hydrochloric Acid → 4,5-Dihydroxy-2-nitrobenzaldehyde

HRID 1982219

Reaction equation

HRID 1982219 reaction equation
ClC[O:3][C:4]1[C:5]([OH:15])=[CH:6][C:7]([N+:12]([O-:14])=[O:13])=[C:8]([CH:11]=1)[CH:9]=[O:10].[Al+3].[Cl-].[Cl-].[Cl-].ClC(Cl)C.Cl>N1C=CC=CC=1>[OH:15][C:5]1[C:4]([OH:3])=[CH:11][C:8]([CH:9]=[O:10])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 63651,1-DichloroethaneHCID 6451240Aluminum(III) ChlorideHCID 114247525-Chloromethoxy-4-hydroxy-2-nitrobenzaldehyde

Product 1

HCID 37823444,5-Dihydroxy-2-nitrobenzaldehydeYield 68.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
47 °C

Procedure

To a stirred, cooled (0° C.) dispersion of 1.52 g (0.00658 mol) of 5-chloromethoxy-4-hydroxy-2-nitrobenzaldehyde (10), 1 g AlCl3, and 10 ml dry dichloroethane, 2.4 ml of dry pyridine are added. During addition, the reaction mixture is protected from atmospheric moisture, and the temperature is kept below 35° C. When addition is complete, the temperature is raised to 47° C., and maintained for 18 hours. 6N HCl is added, keeping the temperature at 30°-35° C., until the mixture is acidic to Congo Red indicator paper. The acidic solution is extracted with diethyl ether, and the combined ether extracts are dried over Na2SO4. After filtration, the ether is removed at reduced pressure, giving 0.82 g (68%) of (1): mp 201°-202°° C.

Workup

  1. additionare added
  2. additionDuring addition
  3. customis kept below 35° C
  4. additionWhen addition
  5. temperaturemaintained for 18 hours
  6. customat 30°-35° C.
  7. extractionThe acidic solution is extracted with diethyl ether
  8. dry with materialthe combined ether extracts are dried over Na2SO4
  9. filtrationAfter filtration
  10. customthe ether is removed at reduced pressure

Sources & evidence

ORD record
ord-23064ba024c24eb897ac24e7430ddb49
Source dataset
uspto-grants-1986_06
Patent number
US04595765

Linked notes

Loading…