Dimethylformamide → Acrylic Acid

Reaction equation

Br[CH2:2]CCCCCCCCCCC[O:14]C1C=C[C:18]([C:19]([O:21]C2C=CC(OC(C)CC)=CC=2)=[O:20])=[CH:17]C=1.[CH3:35][N:36]([CH:38]=O)[CH3:37]>>[C:19]([OH:21])(=[O:20])[CH:18]=[CH2:17].[OH-:14].[CH3:35][N+:36]([CH3:38])([CH3:2])[CH3:37]

Participants

Reactant 2

HCID 6228Dimethylformamide

HCID 197340594-(1-Methylpropoxy)phenyl 4-(12-bromododecyloxy)benzoate

Product 2

HCID 6581Acrylic Acid

HCID 60966Tetramethylammonium hydroxide

Procedure

A solution of 6 mmol (3.2 g) of the bromo compound obtained in (2), 10 mmol (0.72 g) of acrylic acid, and 10 mmol (1.8 g) of tetramethylammonium hydroxide (pentahydrate) in 30 ml of DMF was stirred for 10 hours at room temperature. To the resulting reaction solution was added water and then extracted with ether. The extract was concentrated, and the concentrate was purified by column chromatography to obtain 2.2 g of the objective monomer (3b). (Yield: 71%)

Sources & evidence

ORD record: ord-64dcca14c6b846159878a76c5190a56e
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05269963

Reaction notes

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