Tetrahydrofuran → 2-(Acryloyloxyethoxy)phenol acrylate

HRID 259659

Reaction equation

HRID 259659 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11].C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21].[O:24]1C[CH2:27][CH2:26][CH2:25]1>C1C2NC3C(=CC=CC=3)SC=2C=CC=1>[C:19]([O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][O:1][C:25](=[O:24])[CH:26]=[CH2:27])(=[O:22])[CH:20]=[CH2:21]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 785192-(2-Hydroxyethoxy)phenol

Product 1

HCID 543200612-(Acryloyloxyethoxy)phenol acrylateYield 62%

Reagents, catalysts & solvents 1

HCID 7108PhenothiazineCatalyst

Procedure

A 500-ml, two necked flask was equipped with magnetic stirring bar, nitrogen atmosphere and an addition funnel. The flask was charged with 25 g of 2-(2-hydroxyethoxy)phenol (0.16 mol.), 33 g of triethylamine (0.32 mol.), 250 ml of tetrahydrofuran and 1 g of phenothiazine. Next, 30 g of acryloyl chloride (0.18 mol.) was slowly added to the reaction over 1 hour via the addition funnel. The triethylamine hydrochloride salt was removed by filtration and the mother liquor was evaporated with a rotoevaporator. The remaining liquid was dissolved in chloroform and washed with NaCl(aq.), NH4OH(10%), NaCl(aq.) and dried over MgSO4. The chloroform was removed with a rotoevaporator to yield 26 g (62%) of a reddish brown liquid. The product was confirmed by IR and 13C NMR.

Workup

  1. customA 500-ml, two necked flask was equipped with magnetic stirring bar
  2. customThe triethylamine hydrochloride salt was removed by filtration
  3. customthe mother liquor was evaporated with a rotoevaporator
  4. dissolutionThe remaining liquid was dissolved in chloroform
  5. washwashed with NaCl(aq.), NH4OH(10%), NaCl(aq.)
  6. dry with materialdried over MgSO4
  7. customThe chloroform was removed with a rotoevaporator

Sources & evidence

ORD record
ord-05328384b87746e0b7e8286a48450be6
Source dataset
uspto-grants-1996_06
Patent number
US05523152

Linked notes

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