Acetaldehyde → HCID 23502013, compound

HRID 1835013Notes

Reaction equation

HRID 1835013 reaction equation
[Mg].Br[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1.II.[CH:13](=[O:15])[CH3:14].[Cl-].[NH4+]>O1CCCC1>[OH:15][CH:13]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1)[CH3:14]

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 807IodineHCID 162634-BromostyreneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 23502013HCID 23502013, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This Example illustrates the synthesis of polymeric blocked developer PBDI. First, 4-(1-hydroxyethyl)styrene was prepared. A suspension of 4.82 g (0.198 mol) of magnesium in 200 mL of dry tetrahydrofuran (THF) under nitrogen was treated with 36.3 g (0.198 mmol) of 4-bromostyrene plus a trace of iodine. The reaction, mixture was heated at reflux for 4 h, and then cooled using an ice bath. Acetaldehyde (9.6 g, 0.218 mol) was added, and the mixture was stirred overnight. The reaction mixture was poured onto 300 g of ice plus 25 g of ammonium chloride, and then extracted with ether (3×200 mL). The combined ethereal extracts were concentrated, and the residue was vacuum distilled. The product (17.3 g, 59%) was obtained as a slightly yellow, bp 67-99° C./0.10 mm. 1H NMR (CDCl3) δ 1.50 (d, J=6.4, 3H), 1.8 (br s, 1H), 4.89 (q, J=6.4, 1H), 5.24 (d, J=11.0, 1H), 5.74 (d, J=17.7, 1H), 6.7 (m, 1H), 7.34 (d, J=8.2, 2H), 7.40 (d, J=8.2, 2H).

Workup

  1. customthe synthesis
  2. customThe reaction, mixture
  3. temperaturewas heated
  4. temperatureat reflux for 4 h
  5. temperaturecooled
  6. extractionextracted with ether (3×200 mL)
  7. concentrationThe combined ethereal extracts were concentrated
  8. distillationdistilled

Sources & evidence

ORD record
ord-3789e94631cd4bb4abb35c279e7181d1
Source dataset
uspto-grants-2004_08
Patent number
US06770406B1

Reaction notes

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