2-Methoxybenzaldehyde → HCID 54561133, compound

HRID 1940975Notes

Reaction equation

HRID 1940975 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([CH:17]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])=O.BrC1C=C(Cl)C=CC=1[O:27][CH2:28][O:29][CH2:30][CH2:31]OC.C(=O)[C:35]1[C:36]([O:41]C)=CC=CC=1>>[CH2:30]([O:29][C:28]([C:35]1[C:36](=[O:41])[O:18][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:17][C:6]=2[C:7]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])=[O:27])[CH3:31]

Participants

4

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 21463183HCID 21463183, compoundHCID 21463257HCID 21463257, compound

Product 1

HCID 54561133HCID 54561133, compound

Conditions

Temperature
180 °C

Procedure

A mixture of 5-chloro-2-hydroxy-2'-methoxybenzophenone [prepared from 2-bromo-4-chloro-(2-methoxyethoxy)methoxybenzene and orthoanisaldehyde as the starting materials: melting point, 94°-98° C. (recrystallized from isopropyl ether)](11.8 g), diethyl malonate (13.6 g) and potassium fluoride (2.61 g) was heated at 180° C. for 8.5 hours. After cooling, ethyl acetate was added to the mixture, washed with water, dried and evaporated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane: 1:10) to yield 6-chloro-4-(2-methoxyphenyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester as colorless crystals (7.78 g).

Workup

  1. custompoint, 94°-98° C. (recrystallized from isopropyl ether)](11.8 g), diethyl malonate (13.6 g) and potassium fluoride (2.61 g)
  2. temperatureAfter cooling
  3. additionethyl acetate was added to the mixture
  4. washwashed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-e9ee4c42700d4ce4840cbe81d1d8858f
Source dataset
uspto-grants-1997_12
Patent number
US05700810

Reaction notes

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