Dichloromethane → HCID 18333563, compound

HRID 2269887Notes

Reaction equation

HRID 2269887 reaction equation
[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:13][CH3:14].ClCCl.[C:18]1([C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N+]=[N-])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)(=O)C.CCCCCC>[OH:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([C:6]([O:8][CH:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:7])=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10742Syringic Acid2×HCID 612301,1'-(Diazomethylene)bis(benzene)2×

Product 1

HCID 18333563HCID 18333563, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent2×

Procedure

Combine 4-hydroxy-3,5-dimethoxybenzoic acid (2.0 g, 12.6 mmol) and dichloromethane (200 mL). Add diphenyl diazomethane (2.67 g). After 1 hour, add an additional portion of diphenyl diazomethane (1.2 g). After 1 hour, add 4-hydroxy-3,5-dimethoxybenzoic acid (0.5 g). Concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting sequentially with 20% ethyl acetate/hexane and 50% ethyl acetate/hexane to obtain the diphenylmethyl 4-hydroxy-3,5-dimethoxybenzoate: Rf=0.56 (silica gel, 50% ethyl acetate/hexane).

Workup

  1. waitAfter 1 hour
  2. concentrationConcentrate in vacuo
  3. customto obtain a residue

Sources & evidence

ORD record
ord-e97ebaba5e7d4abdb2d389b85bfa741f
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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