Ammonium Chloride → HCID 13076865, compound

HRID 1506846Notes

Reaction equation

HRID 1506846 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[OH:11].[CH:13]1([Mg]Cl)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[NH4+].[Cl-]>C1COCC1>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([OH:11])=[C:4]([C:3]([CH:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[OH:12])[CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl esterHCID 178478990HCID 178478990, compound

Product 1

HCID 13076865HCID 13076865, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7.0 g of 5-Chloro-2-hydroxy-benzoic acid methyl ester in 38 ml of THF, 115.5 ml of a solution of cyclohexylmagnesium chloride in THF (2 M) was added slowly at room temperature. The reaction mixture was then heated to reflux for 5 h. After cooling to room temperature it was hydrolyzed with ice. Saturated aqueous NH4Cl was added until the white precipitate was dissolved. The aqueous phase was extracted with ether. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was recrystallized from n-heptane to yield a bright yellow product. Yield: 5.2 g.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 5 h
  3. dissolutionwas dissolved
  4. extractionThe aqueous phase was extracted with ether
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was recrystallized from n-heptane
  9. customto yield a bright yellow product

Sources & evidence

ORD record
ord-3ed63e52c9c44c8c8c70f1483753f442
Source dataset
uspto-grants-2015_12
Patent number
US09221784B2

Reaction notes

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