Sulfuric Acid → HCID 67997342, compound

HRID 1908944Notes

Reaction equation

HRID 1908944 reaction equation
[C:1]([O:5][C:6]([C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([C:18]([OH:21])([CH3:20])[CH3:19])([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(Cl)C.[C:26](Cl)(=[O:30])[C:27]([CH3:29])=[CH2:28].S(=O)(=O)(O)O>N1C=CC=CC=1>[C:1]([O:5][C:6]([C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([C:18]([O:21][C:26](=[O:30])[C:27]([CH3:29])=[CH2:28])([CH3:20])[CH3:19])([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 63651,1-DichloroethaneHCID 13528Methacryloyl chlorideHCID 67997339HCID 67997339, compound

Product 1

HCID 67997342HCID 67997342, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

In a flask equipped with a stirrer, a thermometer, a dropping funnel, and a Dimroth condenser, 50 g of 3-(1-hydroxy-1-methylethyl)adamantane-1-carboxylic acid t-butyl ester, 200 mL of dichloroethane, and 80 g of pyridine were put, and 71.7 g of methacrylic acid chloride was dropped thereto at 60° C. over 2 hours. After the dropping was completed, the resultant substance was stirred at 60° C. for another 8 hours. Then, the resultant substance was neutralized with 320 g of 10% aqueous solution of sulfuric acid while the flask was ice-cooled. The reaction solution was separated into an organic layer and a water layer. The organic layer was washed twice with 500 mL of ion exchanged water, and then was concentrated. The obtained raw product was purified by silica gel column chromatography. As a result, 25 g of 3-(1-methacryloyloxy-1-methylethyl)adamantane-1-carboxylic acid t-butyl ester was obtained as a white solid. White solid 2, which was obtained, was identified with 1H-NMR, 13C-NMR and IR (see FIGS. 2, 3 and 4).

Workup

  1. customIn a flask equipped with a stirrer
  2. temperaturecooled
  3. customThe reaction solution was separated into an organic layer
  4. washThe organic layer was washed twice with 500 mL of ion
  5. concentrationwas concentrated
  6. customThe obtained raw product
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f4fac172d69c4b7187caecbfa17347c0
Source dataset
uspto-grants-2013_12
Patent number
US08598292B2

Reaction notes

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