4-Benzyloxy-6-fluoro-3-methyl-naphthalene-2-carbaldehyde → HCID 59326572, compound

HRID 238626Notes

Reaction equation

HRID 238626 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[CH:12]=[C:11]([CH:20]=[O:21])[C:10]=1[CH3:22])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[F:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([CH:20]=[O:21])[C:10]([CH3:22])=[C:9]2[OH:8]

Participants

4

Reactant 1

HCID 593265294-Benzyloxy-6-fluoro-3-methyl-naphthalene-2-carbaldehyde

Product 1

HCID 59326572HCID 59326572, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-benzyloxy-6-fluoro-3-methyl-naphthalene-2-carbaldehyde (165 mg, 0.56 mmol) in ethyl acetate (5 mL) was added 10% palladium on carbon (7 mg). The resulting mixture was stirred vigorously under a hydrogen atmosphere (balloon) for 4 hours, and then filtered. The filtrate was concentrated in vacuo to give 6-fluoro-4-hydroxy-3-methyl-naphthalene-2-carbaldehyde (115 mg, 99%) as a yellow solid which was directly used in the next step without further purification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6262dd8b0ff64a71bd52d0cab5c04325
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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