Methacrolein → HCID 15017966, compound

HRID 2232154Notes

Reaction equation

HRID 2232154 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[N+]=[N-])[CH:6]=[CH:7][CH:8]=1.COC1C=C(C=CC=1)C(=NN)C1C=CC=C(OC)C=1.[O:39]=[CH:40][C:41](=[CH2:43])[CH3:42]>ClCCl.CCCCCCC.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[CH2:42][C:41]2([CH3:43])[CH:40]=[O:39])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 6562MethacroleinHCID 620694HCID 620694, compoundHCID 23051365HCID 23051365, compound

Product 1

HCID 15017966HCID 15017966, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of bis(3-methoxyphenyl)diazomethane, prepared as in Example 84 from 3,3'-dimethoxybenzophenone hydrazone (18.7 g) and activated manganese dioxide (24.3 g) in dichloromethane (125 mL) was added to a solution of methacrolein (10.8 mL) in heptane (70 mL) over 10 minutes at 40° C. The mixture was stirred at 40° C. for 16 hours, and then after the dichloromethane was distilled off, at 85° C. for 1 hour. The solvent was removed in vacuo and the residue was purified by HPLC (ethyl acetate-hexane; 1:5) to yield 8.0 g of 2,2-bis(3-methoxyphenyl)1-methylcyclopropanecarboxaldehyde. Crystallization of the material from ethyl acetate-hexane provided 6.2 g of the aldehyde, mp 122°-123° C.

Workup

  1. distillationafter the dichloromethane was distilled off, at 85° C. for 1 hour
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by HPLC (ethyl acetate-hexane; 1:5)

Sources & evidence

ORD record
ord-fe829752ce49409ab8e5666863e09bb1
Source dataset
uspto-grants-1988_11
Patent number
US04786646

Reaction notes

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