Chloride → (9H-Fluoren-9-yl)methyl 2-methylprop-2-enoate

HRID 2290790Notes

Reaction equation

HRID 2290790 reaction equation
[Cl-].[CH:2]1[C:14]2[CH:13]([CH2:15][OH:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[O:17]1[CH2:21][CH2:20][CH2:19]C1.[CH2:22](N(CC)CC)C>>[C:21]([O:16][CH2:15][CH:13]1[C:14]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=2[C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:17])[C:20]([CH3:22])=[CH2:19]

Participants

5

Reactant 4

HCID 312ChlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 904669H-Fluorene-9-methanol

Product 1

HCID 13796917(9H-Fluoren-9-yl)methyl 2-methylprop-2-enoateYield 10%

Procedure

Methacrloyl chloride (5 ml) was added dropwise to a cooled solution of 9-fluorene methanol (Aldrich Chemical Co. 5.04g, 0.026 moles) in a mixture of dry tetrahydrofuran (15 ml) and dry triethylamine (10 ml). After 1 hour at 0° C. the reaction was quenched with water and extracted with ether. The resultant oil was flash chromatographed to give 0.70g, (10% yield) of (9-fluorenyl)-methyl methacrylate (9 FMMA) as a light yellow oil. The original monomer stored at 0° C. polymerized over a period of 3 days. This material was dissolved in and added dropwise to hexane, yielding a precipitate of poly(9 FMMA) ([η]=0.28 dl/g).

Workup

  1. customAfter 1 hour at 0° C. the reaction was quenched with water
  2. extractionextracted with ether
  3. customchromatographed

Sources & evidence

ORD record
ord-4a00e74bbef44cd18f9bb5459fc1bff0
Source dataset
uspto-grants-1986_10
Patent number
US04618566

Reaction notes

Loading…