Acetic Acid → HCID 21867987, compound

HRID 2056231Notes

Reaction equation

HRID 2056231 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[S:7]([CH2:11][CH2:12][OH:13])[CH2:8][CH2:9][OH:10].C(N(CC)CC)C.C(O)(=O)C>ClCCl>[C:1]([O:10][CH2:9][CH2:8][S:7][CH2:11][CH2:12][OH:13])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5447ThiodiglycolHCID 8471Triethylamine2×HCID 13528Methacryloyl chloride

Product 1

HCID 21867987HCID 21867987, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methacryloyl chloride (16.7 g; 0.160 mol) in dichloromethane (100 ml) was added dropwise at 5° C. to a solution of thiodiethanol (20 g; 0.164 mol) and triethylamine (33.7 g; 0.334 mol) in dichloromethane (50 ml). After addition was complete, the solution was stirred at ambient temperature for 16 hrs. The excess triethylamine was neutralised with glacial acetic acid and the volume reduced on a rotary evaporator. The soluble organic products were extracted in diethyl ether and separated by filtration. Thiodiethanol monomethacrylate was purified by preparative flash chromatography, using silica gel (eluant=1:1 diethyl ether:hexane). Fractions containing pure product were collected and combined to yield thiodiethanol monomethacrylate (8.5 g; 0.044 mol, 28% yield) as a light coloured oil. Several attempts at distillation of TEDMA at reduced pressure and in the presence of excess stabiliser resulted in rapid polymerisation of the monomer. Thiodiethanol monomethacrylate was stored at 4° C. in the presence of 100 ppm 3,5-di-tert-butylcatechol.

Workup

  1. additionAfter addition
  2. customthe volume reduced on a rotary evaporator
  3. extractionThe soluble organic products were extracted in diethyl ether
  4. customseparated by filtration
  5. customThiodiethanol monomethacrylate was purified by preparative flash chromatography
  6. additionFractions containing pure product
  7. customwere collected

Sources & evidence

ORD record
ord-43dcad4e5511420391dee7a4e9844a0b
Source dataset
uspto-grants-2008_02
Patent number
US07335306B2

Reaction notes

Loading…