Hydrochloric Acid → 3-(4-Fluoro-3-methoxyphenyl)prop-2-enoic acid

HRID 2100722Notes

Reaction equation

HRID 2100722 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].Cl>N1C=CC=CC=1.N1CCCCC1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:13][C:14]([OH:16])=[O:15])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 27373584-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 534043133-(4-Fluoro-3-methoxyphenyl)prop-2-enoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8082PiperidineSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-Fluoro-3-methoxy-benzaldehyde (6.16 g, 40 mmol), and malonic acid (6.24 g, 60 mmol) in pyridine (30 ml) and piperidine (1 ml) was heated at 120° C. for 2 hrs. The mixture was cooled to room temperature and neutralized with concentrated HCl to PH<3, the white solid was collected and dried to give 7.6 g of product (97% yield). LC-MS: m/e 195 (M−1)

Workup

  1. customthe white solid was collected
  2. customdried

Sources & evidence

ORD record
ord-7c2cf292a17f448dae2c111e5cf6b23e
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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