Octane → 1-ADAMANTYL ACRYLATE

HRID 1916014Notes

Reaction equation

HRID 1916014 reaction equation
[C:1]12([OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3](O)([CH2:4]3)[CH2:2]1)[CH2:8]2.[Na].CCCCCCCC.[C:22](O)(=[O:25])[CH:23]=[CH2:24]>S(=O)(=O)(O)O.COC1C=CC(O)=CC=1.O.C1(C)C=CC=CC=1>[C:22]([O:12][C:1]12[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2)(=[O:25])[CH:23]=[CH2:24]

Participants

9

Reactant 4

HCID 356OctaneHCID 6581Acrylic AcidHCID 5738291,3-AdamantanediolHCID 5360545Sodium

Product 1

HCID 113901281-ADAMANTYL ACRYLATEYield 79.2%

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidCatalystHCID 90154-MethoxyphenolCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

Adamantyl acrylate is synthesized by the method described in JP-2001-106650-A. That is, 86.4 g (513 mmol) of 1,3-adamantane diol containing sodium in an amount of 0.05% by weight, 400 ml of toluene, 400 ml of n-octane, 108 g (1,500 mmol) of acrylic acid, 1.23 g of strong sulfuric acid, and 0.37 g p-methoxyphenol are placed in a separable flask equipped with a stirrer, a thermometer, a Dean-Stark water separator, a Dimroth condenser, an air introduction tube, and a separating valve provided on the bottom side. Reaction is conducted for five hours in a reflux state at 112° C. while inspiring a small amount of air to the flask. During the reaction, produced water is removed by using the Dean-Stark water separator. The reaction liquid is cooled down to room temperature followed by filtration of insoluble matters. 840 g of 5% by weight sodium hydroxide solution is admixed and separated. Thereafter, the organic phase is washed with 400 ml of water six times. The organic phase is condensed with a reduced pressure, filtered, and dried to obtain 83.8 g of adamantyl acrylate of white powder.

Workup

  1. customAdamantyl acrylate is synthesized by the method
  2. customare placed in a separable flask
  3. customequipped with a stirrer
  4. customReaction
  5. customDuring the reaction
  6. customis removed
  7. customThe reaction liquid
  8. filtrationfollowed by filtration of insoluble matters
  9. customseparated
  10. washThereafter, the organic phase is washed with 400 ml of water six times
  11. customcondensed with a reduced pressure
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-eac53207ef6344e0bfeab26cca3dc5c0
Source dataset
uspto-grants-2013_12
Patent number
US08617778B2

Reaction notes

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