Ammonium Chloride → HCID 11959804, compound

HRID 1866835Notes

Reaction equation

HRID 1866835 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:11]([Mg]Cl)=[CH2:12].C1COCC1.C1(C)C=CC=CC=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[OH:5][CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([CH3:10])[C:2]=1[OH:1])[CH:11]=[CH2:12]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5227773-MethylsalicylaldehydeHCID 22635083Tetrahydrofuran tolueneHCID 178461836HCID 178461836, compound

Product 1

HCID 11959804HCID 11959804, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
17.5 °C

Procedure

2-Hydroxy-3-methylbenzaldehyde (48.78 g, purity: 40.7%, 0.146 mol) was dissolved in toluene (100 ml), and the mixture was added to a reactor under a nitrogen atmosphere. After the mixture was cooled to 0° C. in ice-water, a solution of vinyl magnesium chloride in THF-toluene (1.77M, 182 ml, 0.32 mol, THF:toluene=1:1 (v:v)) was added thereto over 15 minutes such that the temperature of the mixture did not exceed 25° C. After the mixture was stirred at 15-20° C. for 2 hours, it was cooled to 0° C. A 20% aqueous ammonium chloride solution (250 ml) was added thereto. After the mixture was stirred at 25° C. for 1 hour, the solution was separated. The organic layer was concentrated to obtain 32.36 g (purity: 73.5%, 0.145 mol) of 2-(1-hydroxy-2-propenyl)-6-methylphenol as an orange-colored oil.

Workup

  1. additionthe mixture was added to a reactor under a nitrogen atmosphere
  2. temperatureit was cooled to 0° C
  3. stirringAfter the mixture was stirred at 25° C. for 1 hour
  4. customthe solution was separated
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-3f70313acafb437aad0244071921af9a
Source dataset
uspto-grants-2009_12
Patent number
US07629494B2

Reaction notes

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