N,N-Dimethylaniline → HCID 69618714, compound

HRID 859812Notes

Reaction equation

HRID 859812 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22]O)=[C:16]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[CH:15]=[CH:14][C:8]=1[CH:9]=[CH:10][C:11]([OH:13])=[O:12].[C:30](Cl)(=[O:33])[CH:31]=[CH2:32].CN(C)[C:37]1C=CC=C[CH:38]=1.O1CC[CH2:46][CH2:45]1>>[CH2:5]([O:6][C:7]1[C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:45][CH3:46])=[C:16]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:33])[CH:31]=[CH2:32])[CH:15]=[CH:14][C:8]=1[CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH2:4][CH2:3][CH2:2][CH2:37][CH3:38]

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 8028TetrahydrofuranHCID 13140Acryloyl chlorideHCID 69618831HCID 69618831, compound

Product 1

HCID 69618714HCID 69618714, compoundYield 86%

Conditions

Temperature
60 °C

Procedure

Into a three-neck flask, 2,3,4-tri(4-hydroxy-butyloxy)cinnamic acid (6.2 g), acrylic acid chloride (1.3 ml), N,N-dimethylaniline (2.1 g) and 100 mL of tetrahydrofuran were added and stirred at 60° C. for 5 hours. After cooling, the reaction solution was extracted with ethyl and washed with water. The extract was concentrated and then purified by column chromatography to obtain the titled compound (6.0 g). Yield: 86%.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction solution was extracted with ethyl
  3. washwashed with water
  4. concentrationThe extract was concentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-93c98f3d391648f59c7f423a9a5179fd
Source dataset
uspto-grants-2006_12
Patent number
US07153548B2

Reaction notes

Loading…