Sulfuric Acid → 6-(22-Hydroxydocosyl)-2,3-dimethoxy-5-methylphenol

HRID 637885Notes

Reaction equation

HRID 637885 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[C:4]([CH3:12])[C:3]=1[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][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34](OC)=[O:35].[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>O1CCCC1>[OH:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:3]1[C:2]([OH:1])=[C:7]([O:8][CH3:9])[C:6]([O:10][CH3:11])=[CH:5][C:4]=1[CH3:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 12824096HCID 12824096, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 128241256-(22-Hydroxydocosyl)-2,3-dimethoxy-5-methylphenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoate (3 g) in tetrahydrofuran (30 ml) is added lithium aluminum hydride and the mixture is stirred at room temperature for 1 hour. Under ice-cooling, 10% aqueous solution of sulfuric acid is added to the reaction mixture. The mixture is subjected to extraction with ether. The extract is washed with water and dried. The solvent is distilled off under reduced pressure, whereby 6-(22-hydroxydocosyl)-2,3-dimethoxy-5-methylphenol is obtained as colorless needles. m.p. 78° C.-81° C.

Workup

  1. temperatureUnder ice-cooling
  2. extractionThe mixture is subjected to extraction with ether
  3. washThe extract is washed with water
  4. customdried
  5. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-91b74e34e9134ad19d30f0b636f29b2d
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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