Hydrochloric Acid → 21-(2-Hydroxy-3,4-dimethoxy-6-methylbenzoyl)heneicosanoic acid

HRID 1903421Notes

Reaction equation

HRID 1903421 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[O:7].[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH3:44])[CH:37]=[C:38]([O:42]C)[C:39]=1[O:40][CH3:41].Cl>[N+](C1C=CC=CC=1)([O-])=O.O>[OH:42][C:38]1[C:39]([O:40][CH3:41])=[C:34]([O:33][CH3:32])[CH:35]=[C:36]([CH3:44])[C:37]=1[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 809223,4,5-TrimethoxytolueneHCID 6451240Aluminum(III) ChlorideHCID 20431167Methyl 21-chloroformylheneicosanoate

Product 1

HCID 1282407121-(2-Hydroxy-3,4-dimethoxy-6-methylbenzoyl)heneicosanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7416NitrobenzeneSolvent

Procedure

Aluminum chloride (2.5 g) is added portionwise in a nitrogen atmosphere to a solution of 1 g of methyl 21-chloroformylheneicosanoate and 1.7 g of 3,4,5-trimethoxytoluene in 50 ml of nitrobenzene, and the resulting mixture is stirred at room temperature for 48 hours. To the reaction mixture are added water and diluted hydrochloric acid, and the whole mixture is extracted with ether. After distilling of the solvent, the residue is dissolved in methanol, 4.6 ml of a 30% sodium hydroxide solution is added, and the mixture is stirred at 60° C. for an hour. The reaction mixture is washed with ether, then made acidic with diluted hydrochloric acid and extracted with ethyl acetate. The extract is washed with water and dried, the solvent distilled off, and the residue chromatographed on silica gel. The crystals recovered from the chloroform-ethanol (17:1) eluate are recrystallized from ether-hexane to give colorless crystals of 21-(2-hydroxy-3,4-dimethoxy-6-methylbenzoyl)heneicosanoic acid. m.p. 103°-150° C.

Workup

  1. extractionthe whole mixture is extracted with ether
  2. distillationAfter distilling of the solvent
  3. dissolutionthe residue is dissolved in methanol
  4. addition4.6 ml of a 30% sodium hydroxide solution is added
  5. stirringthe mixture is stirred at 60° C. for an hour
  6. washThe reaction mixture is washed with ether
  7. extractionextracted with ethyl acetate
  8. washThe extract is washed with water
  9. customdried
  10. distillationthe solvent distilled off
  11. customthe residue chromatographed on silica gel
  12. customThe crystals recovered from the chloroform-ethanol (17:1) eluate
  13. customare recrystallized from ether-hexane

Sources & evidence

ORD record
ord-8c328956ae354663bed3f71eb97b569f
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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