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

HRID 1903424Notes

Reaction equation

HRID 1903424 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 30 ml of a solution of 3 g of methyl 22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoate in tetrahydrofuran is added lithium aluminum hydride, and the mixture is stirred at room temperature for 1 hour. To the reaction mixture is added 10% sulfuric acid under ice cooling, and the whole mixture is extracted with ether. The extract is washed with water and dried, and then the solvent is distilled off under reduced pressure to give colorless crystals of 6-(22-hydroxydocosyl)-2,3-dimethoxy-5-methylphenol.

Workup

  1. extractionthe whole mixture is extracted with ether
  2. washThe extract is washed with water
  3. customdried
  4. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-b5fadfd1ff434de2b7992b5822f2ffda
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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