Water → HCID 86669344, compound

HRID 1844530Notes

Reaction equation

HRID 1844530 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]([CH:14]=[O:15])[CH:11]=[C:10]([O:16]CC)[C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].O.CCOC(C)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]([CH:14]=[O:15])[CH:11]=[C:10]([OH:16])[C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 86681500HCID 86681500, compound

Product 1

HCID 86669344HCID 86669344, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of methyl 2,6-diethoxy-4-formylbenzoate (950 mg, 3.8 mmol) and AlCl3 (1.0 g, 7.6 mmol) in anhydrous DCM (30 mL) was stirred at 10° C. for 5 minutes. The resulting mixture was poured into water (100 mL) followed by a standard aqueous/EtOAc workup. The residue was purified by column chromatography on silica gel (PE:EtOAc=10:1) to give Intermediate 8 as off-white solid (500 mg, yield 59%).

Workup

  1. customThe residue was purified by column chromatography on silica gel (PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-208d2615ce284ae98a2cf353e9fc53ef
Source dataset
uspto-grants-2015_02
Patent number
US08946434B2

Reaction notes

Loading…