Sulfuric Acid → Adapalene methyl ester

HRID 2051086Notes

Reaction equation

HRID 2051086 reaction equation
C(O[C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)(=O)C.C1CCCCC1.S(=O)(=O)(O)O.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:35]=[C:36]3[C:41](=[CH:42][CH:43]=2)[CH:40]=[C:39]([C:44]([O:46][CH3:47])=[O:45])[CH:38]=[CH:37]3)=[CH:30][CH:29]=1>C(O)C>[C:5]12([C:29]3[CH:30]=[C:31]([C:34]4[CH:35]=[C:36]5[C:41](=[CH:42][CH:43]=4)[CH:40]=[C:39]([C:44]([O:46][CH3:47])=[O:45])[CH:38]=[CH:37]5)[CH:32]=[CH:33][C:28]=3[O:27][CH3:26])[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8078CyclohexaneHCID 5199731-Adamantyl acetateHCID 19834503Methyl 6-(4-methoxyphenyl)-2-naphthoate

Product 1

HCID 10526466Adapalene methyl esterYield 68.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 ml three-necked flask, are placed 1 g of 1-acetoxyadamantane and 50 ml of cyclohexane in a nitrogen environment. After total dissolution, 0.25 g of concentrated sulfuric acid is added drop by drop and 1 g of methyl 6-(4-methoxyphenyl)-2-naphthoate is added slowly. After leaving in vigorous agitation for 48 hours, 20 ml of denatured ethanol are added and the mixture is agitated for 2 hours. The solid obtained is filtered with sintered glass and washed abundantly with water until neutrality is reached. After drying at 30° C. for 24 hours in a vacuum oven, 1 g of desired raw product was obtained (Melting point: 221°-227° C.).

Workup

  1. customIn a 100 ml three-necked flask, are placed
  2. additionis added slowly
  3. customAfter leaving in vigorous agitation for 48 hours
  4. customThe solid obtained
  5. filtrationis filtered with sintered glass
  6. washwashed abundantly with water until neutrality
  7. customAfter drying at 30° C. for 24 hours in a vacuum oven

Sources & evidence

ORD record
ord-f8a729500885415ab2d64ef7873f60ec
Source dataset
uspto-grants-1991_05
Patent number
US05015758

Reaction notes

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