Formamide → 2-(6-Methoxy-2-naphthyl)propionic acid

HRID 2290945Notes

Reaction equation

HRID 2290945 reaction equation
Br[CH:2]([C:4]1([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[CH:10]=2)OCCO1)C.[C:21](=O)([O-:23])[O-:22].[Ca+2].C(N)=O>>[CH3:20][O:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH:4]([CH3:2])[C:21]([OH:23])=[O:22])[CH:18]=[CH:17]2

Participants

4

Reactant 3

HCID 713FormamideHCID 10112Calcium CarbonateHCID 15908760HCID 15908760, compound

Product 1

HCID 13022-(6-Methoxy-2-naphthyl)propionic acidYield 30%

Conditions

Temperature
140 °C

Procedure

A mixture of 2(1-bromoethyl)-2-(6-methoxy-2-naphthyl)-1,3-dioxolane (0.84 g; 2.5 mmol), calcium carbonate (0.3 g; 3 mmol) and formamide (5 ml) is heated at 140° C. under stirring for 1 h. The mixture is worked up as described in example 1a to provide 2-(6-methoxy-2-naphthyl)-propionic acid (0.172 g; 0.75 mmol; yield 30%), m.p. 154°-155° C.

Sources & evidence

ORD record
ord-2cfe56f1c32c46f0b2c36e80bacb0c2e
Source dataset
uspto-grants-1986_10
Patent number
US04618697

Reaction notes

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