Methacrylic Acid → 3-Hydroxy-1-adamantyl acrylate

HRID 1019479Notes

Reaction equation

HRID 1019479 reaction equation
[C:1]([OH:6])(=[O:5])[C:2](C)=[CH2:3].[OH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10](C=C(C)C([O-])=O)([CH2:11]3)[CH2:9]1)[CH2:15]2.C1C2C(=CC3C(C=2COC(=O)C(C)=C)=CC=CC=3)C=CC=1.CC(C)C#N>O1CCCC1>[CH2:3]=[CH:2][C:1]([O:6][C:10]12[CH2:9][C:8]3([OH:7])[CH2:17][CH:12]([CH2:13][CH:14]([CH2:15]3)[CH2:16]1)[CH2:11]2)=[O:5]

Participants

6

Reactant 4

HCID 4093Methacrylic AcidHCID 6559IsobutyronitrileHCID 36187549-Anthrylmethyl methacrylateHCID 1317313693-Hydroxy-1 adamantylmethacrylate

Product 1

HCID 222287903-Hydroxy-1-adamantyl acrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methacrylic acid (0.775 g, 9 mmol), 3-hydroxy-1 adamantylmethacrylate (1.42 g, 6 mmol), 9-anthrylmethylmethacrylate (1.38 g, 5 mmol) in 20 mL of tetrahydrofuran (THF) was added 2,2′-azobis(2-methylpropionitrile (0.16 g, 1 mmol). The resulting solution was purged by nitrogen for 30 minutes before it was heats to 72° C. for 18 hours under nitrogen. The solution was then cooled to room temperature and added drop-wise into 400 mL of de-ionized water. The solid was filtered with a frit funnel, washed with water (2×200 ml) and dried in a vacuum oven at 50° C. for 24 hours to afford 3.1 gram of P1 as white solid.

Workup

  1. additionwas added
  2. customThe resulting solution was purged by nitrogen for 30 minutes before it
  3. customto 72° C.
  4. customfor 18 hours
  5. additionadded drop-wise into 400 mL of de-ionized water
  6. filtrationThe solid was filtered with a frit funnel
  7. washwashed with water (2×200 ml)
  8. customdried in a vacuum oven at 50° C. for 24 hours
  9. customto afford 3.1 gram of P1 as white solid

Sources & evidence

ORD record
ord-77bd4faca56641d7918889d62309813e
Source dataset
uspto-grants-2014_05
Patent number
US08715907B2

Reaction notes

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