1,2-Dichloroethane → 1,3-Adamantanedicarboxylic acid

HRID 1793242Notes

Reaction equation

HRID 1793242 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][C:14]([OH:22])([CH2:15]3)[CH2:13]1)[CH2:19]2.ClCCCl.S(=O)(=O)(O)[OH:28].[CH:32]([OH:34])=[O:33]>>[OH:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][C:14]([OH:22])([CH2:15]3)[CH2:13]1)[CH2:19]2.[C:1]12([C:14]([OH:22])=[O:28])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([C:32]([OH:34])=[O:33])([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 284Formic AcidHCID 1118Sulfuric AcidHCID 9238AdamantaneHCID 5738291,3-Adamantanediol

Product 2

HCID 643391,3-Adamantanedicarboxylic acidHCID 5738291,3-Adamantanediol

Procedure

The synthesis of 2-methacryloyloxy-2-(3-(2-hydroxy-2-propyl)1-1-adamantyl)propane was performed by the following method. First, according to the method described in Japanese Patent Application Laid-open No. 2002-167342, 1000 g of 1,3-dihydroxyadamantane was synthesized from adamantane. Next, a four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a Dimroth condenser was charged with 100 g of 1,3-dihydroxyadamantane, 500 mL of 1,2-dichloroethane and 800 g of 96% sulfuric acid, and further 300 g of formic acid was dropped into the flask for 1 h. Thereafter, the contents of the flask were reacted at 25° C. for 10 h. The resultant reaction solution was filtered to separate precipitated crystals therefrom. The thus separated crystals were washed with water to obtain 140 g of 1,3-adamantanedicarboxylic acid. Then, a four-necked flask equipped with a stirrer, a thermometer and a Dimroth condenser was charged with 140 g of 1,3-adamantanedicarboxylic acid, 12 g of 96% sulfuric acid, 200 g of methanol and 1000 mL of 1,2-dichloroethane, and the contents of the flask were reacted at 62° C. for 10 h.

Workup

  1. customNext, a four-necked flask equipped with a stirrer
  2. additionwas dropped into the flask for 1 h
  3. customThereafter, the contents of the flask were reacted at 25° C. for 10 h
  4. customThe resultant reaction solution
  5. filtrationwas filtered
  6. customto separate
  7. customprecipitated crystals
  8. washThe thus separated crystals were washed with water

Sources & evidence

ORD record
ord-198625e865c349d6bf36a744738e8613
Source dataset
uspto-grants-2006_07
Patent number
US07078562B2

Reaction notes

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