Methacrylic Acid → 3-Hydroxy-1-adamantyl acrylate

HRID 1464875

Reaction equation

HRID 1464875 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

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 (0.24 g, 1.5 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-cf5bd68e4ca64d168919decaff0f9313
Source dataset
uspto-grants-2015_04
Patent number
US08999624B2

Linked notes

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