Acetate → HCID 54069922, compound

HRID 840538Notes

Reaction equation

HRID 840538 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1C=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:24][CH3:25])(=[O:23])[CH2:18][C:19]([O:21][CH3:22])=[O:20].[C:26]([O-])(=O)C>C1C=CC=CC=1>[CH3:22][O:21][C:19](=[O:20])[C:18](=[CH:26][C:14]1[CH:13]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:16][CH:15]=1)[C:17]([O:24][CH3:25])=[O:23]

Participants

5

Reactant 3

HCID 175AcetateHCID 7943Dimethyl malonateHCID 3447842-(Benzyloxy)benzaldehyde

Product 1

HCID 54069922HCID 54069922, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of benzyloxybenzaldehyde (10.6 g, 50.0 mmol) and dimethyl malonate (6.6 g, 50.0 mmol) in benzene (100 mL) containing a catalytic quantity of pipiridinium acetate was refluxed in a Dean-Stark trap for 16 h. After cooling to room temperature, the solution was concentrated. The residue was crystallised from ethyl acetate/heptane to give 14.5 g (90%) of 2-(4-benzyloxy-benzylidene)-malonic acid dimethyl ester: mp 134-135° C. 1H NMR (300 MHz, CDCl3): δ3.82 (s, 3H), 3.86 (s, 3H), 5.08 (s, 2H), 6.95 (d, 2H), 7.30-7.45 (m, 7H), 7.70 (s, 1H)

Workup

  1. temperaturewas refluxed in a Dean-Stark trap for 16 h
  2. concentrationthe solution was concentrated
  3. customThe residue was crystallised from ethyl acetate/heptane

Sources & evidence

ORD record
ord-6aa89a9f6b4f46959bf75ac49ab2281a
Source dataset
uspto-grants-2002_04
Patent number
US06369055B1

Reaction notes

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