Acrylic Acid → 4-(3-Acryloxy-2-hydroxypropoxy)-1,2,2,6,6-pentamethylpiperidine

HRID 1736611Notes

Reaction equation

HRID 1736611 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[N:8]([CH3:13])[C:7]([CH3:15])([CH3:14])[CH2:6]1.[C:17]([OH:21])(=[O:20])[CH:18]=[CH2:19]>C1(C)C(C)=CC=CC=1.[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[C:17]([O:21][CH2:16][CH:2]([OH:1])[CH2:3][O:4][CH:5]1[CH2:6][C:7]([CH3:14])([CH3:15])[N:8]([CH3:13])[C:9]([CH3:12])([CH3:11])[CH2:10]1)(=[O:20])[CH:18]=[CH2:19]

Participants

5

Reactant 2

HCID 6581Acrylic AcidHCID 142745051,2,2,6,6-Pentamethyl-4-(oxiran-2-ylmethoxy)piperidine

Product 1

HCID 539088494-(3-Acryloxy-2-hydroxypropoxy)-1,2,2,6,6-pentamethylpiperidineYield 43%

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 7237O-XyleneSolvent

Procedure

375 g (1.65 mol of (4-(2,3-epoxypropoxy)-1,2,2,6,6-pentamethylpiperidine (=A1a) in 1.5 l of xylene are introduced under argon into a 2.5 l sulfonation flask fitted with magnetic stirrer, thermometer and condenser. 108 g (1.5 mol) of acrylic acid and 27.8 g (75 mmol) of ethyltriphenylphosphonium bromide are added. The reactants are allowed to react at 70° C. for 18 hours. The cooled product is poured into ice water, and the organic phase is separated off, washed twice with 1N sodium hydroxide solution, dried and evaporated. The residue is distilled over a short Vigreux column. 193 g (43%) of the title product are obtained as a clear liquid of boiling point 119°-125° C. (0.06 mm Hg).

Workup

  1. customfitted with magnetic stirrer
  2. customto react at 70° C. for 18 hours
  3. customthe organic phase is separated off
  4. washwashed twice with 1N sodium hydroxide solution
  5. customdried
  6. customevaporated
  7. distillationThe residue is distilled over a short Vigreux column

Sources & evidence

ORD record
ord-46312a67667a41469d4fd6e48553fe92
Source dataset
uspto-grants-1996_07
Patent number
US05541274

Reaction notes

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