Hydrochloric Acid → 7-Chloro-3-hydroxymethyl-2-methyl-naphthalen-1-ol

HRID 1468334

Reaction equation

HRID 1468334 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18](O)=[O:19])[C:12]([CH3:21])=[C:11]2[OH:22].Cl>O1CCCC1>[Cl:7][C:8]1[CH:9]=[C:10]2[C:15]([CH:14]=[C:13]([CH2:18][OH:19])[C:12]([CH3:21])=[C:11]2[OH:22])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 593265616-Chloro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid

Product 1

HCID 593264967-Chloro-3-hydroxymethyl-2-methyl-naphthalen-1-olYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a slurry of lithium aluminum hydride (4.1 g, 108 mmol) in tetrahydrofuran (80 mL) was added a solution of 6-chloro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid (12.7 g, 54 mmol) in tetrahydrofuran (80 mL) at 0° C. under a nitrogen atmosphere. After being heated at 60° C. for 5 hours, the resulting mixture was cooled to 0° C. and treated with 1 N hydrochloric acid to quench the reaction. The aqueous layer was extracted with ethyl acetate (100 mL×4). The combined organic layers were washed with brine (200 mL×2), dried over sodium sulfate and concentrated in vacuo to give 7-chloro-3-hydroxymethyl-2-methyl-naphthalen-1-ol (8.5 g, 71%) as a white solid.

Workup

  1. temperaturethe resulting mixture was cooled to 0° C.
  2. customto quench
  3. customthe reaction
  4. extractionThe aqueous layer was extracted with ethyl acetate (100 mL×4)
  5. washThe combined organic layers were washed with brine (200 mL×2)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ae2b0a9b2f9497e8001d2c579c3c7dd
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Linked notes

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