Acetonitrile → 4-(6-Acryloyloxyhexyloxy)benzaldehyde

HRID 1654553Notes

Reaction equation

HRID 1654553 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.C(N(CC)CC)C.C(#N)C.[C:27](Cl)(=[O:30])[CH:28]=[CH2:29]>O>[C:27]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]=[O:14])=[CH:15][CH:16]=1)(=[O:30])[CH:28]=[CH2:29]

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 150510824-(6-Hydroxyhexoxy)benzaldehyde

Product 1

HCID 196022174-(6-Acryloyloxyhexyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

8.9 g (0.04 mol) of 4-(6-hydroxyhexyloxy)benzaldehyde, 6.8 ml of triethylamine and 100 ml of acetonitrile were put in a three-neck flask equipped with a thermometer and a stirrer and cooled to 0° C. To this mixture was dropwise added a solution comprising 4.0 g (0.044 mol) of acryloyl chloride and 10 ml of acetonitrile with stirring at 0° C. to 5° C. After the addition, the whole mixture was stirred for one hour at 0° C. and poured into water containing ice. The crystals which precipitated out after a while were taken out by filtration, washed with water and dried by airing to obtain the intended compound. The yield of the product was 3.94 g (35.7%). The product had a melting point of 30° C. or lower.

Workup

  1. customequipped with a thermometer and a stirrer
  2. additionAfter the addition
  3. stirringthe whole mixture was stirred for one hour at 0° C.
  4. additioncontaining ice
  5. customThe crystals which precipitated out after a while
  6. filtrationwere taken out by filtration
  7. washwashed with water
  8. customdried
  9. customto obtain the intended compound

Sources & evidence

ORD record
ord-c76380395ec44470a2b47e867b1373d6
Source dataset
uspto-grants-1995_04
Patent number
US05408009

Reaction notes

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