Carbon Tetrachloride → 7-Chloro-3-chloromethyl-2-methyl-naphthalen-1-ol

HRID 1468335Notes

Reaction equation

HRID 1468335 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Cl:24])(Cl)(Cl)Cl.[Cl:25][C:26]1[CH:35]=[C:34]2[C:29]([CH:30]=[C:31](CO)[C:32]([CH3:37])=[C:33]2[OH:36])=[CH:28][CH:27]=1>O1CCCC1>[Cl:25][C:26]1[CH:35]=[C:34]2[C:29]([CH:30]=[C:31]([CH2:20][Cl:24])[C:32]([CH3:37])=[C:33]2[OH:36])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 593264967-Chloro-3-hydroxymethyl-2-methyl-naphthalen-1-ol

Product 1

HCID 593264827-Chloro-3-chloromethyl-2-methyl-naphthalen-1-olYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (20 g, 76 mmol) in anhydrous tetrahydrofuran (165 mL) was added carbon tetrachloride (50 mL). After the mixture was stirred at room temperature for 20 minutes, 7-chloro-3-hydroxymethyl-2-methyl-naphthalen-1-ol (8.4 g, 37.7 mmol) was added as a solid under a nitrogen atmosphere. After being stirred at reflux for 2 hours, the resulting mixture was cooled to room temperature, and concentrated in vacuo. The residue was purified by column chromatography (elution with 5% ethyl acetate in petroleum ether) to afford 7-chloro-3-chloromethyl-2-methyl-naphthalen-1-ol (8.7 g, 96%) as a white solid.

Workup

  1. stirringAfter being stirred
  2. temperatureat reflux for 2 hours
  3. temperaturethe resulting mixture was cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (elution with 5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-d167d5ac6a2445f88b155ce8dedd20bc
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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