Tetrahydrofuran → Phenyl acrylate

HRID 3067

Reaction equation

HRID 3067 reaction equation
OCCO[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1O.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21].[O:24]1CCCC1>C1C2NC3C(=CC=CC=3)SC=2C=CC=1>[C:19]([O:22][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:24])[CH:20]=[CH2:21]

Participants

6

Reactant 4

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

Product 1

HCID 61242Phenyl 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-81a231be09734e50823c3b6abac323f1
Source dataset
uspto-grants-1998_03
Patent number
US05733648

Linked notes

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