Acetyl chloride → 1-(1-Hydroxy-4-methoxynaphthalen-2-yl)ethan-1-one

HRID 2054548Notes

Reaction equation

HRID 2054548 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([OH:13])=[CH:5][CH:4]=1.[C:14](Cl)(=[O:16])[CH3:15]>C1(C)C=CC=CC=1.[N+](C)([O-])=O.C(Cl)Cl.[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[C:14]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[OH:13])(=[O:16])[CH3:15]

Participants

7

Reactant 2

HCID 6367Acetyl chlorideHCID 665424-Methoxy-1-naphthol

Product 1

HCID 109000401-(1-Hydroxy-4-methoxynaphthalen-2-yl)ethan-1-oneYield 72%

Reagents, catalysts & solvents 4

HCID 2734571Scandium(III) triflateCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 6375NitromethaneSolvent

Procedure

A solution of 4-methoxy-1-naphthol 11 (435 mg, 2.5 mmol) in toluene (5 mL) and nitromethane (0.75 mL) was treated with scandium triflate (61.52 mg, 0.125 mmol) and acetyl chloride (0.195 mL, 2.75 mmol) and irradiated in the microwave reactor (Personal Chemistry, Inc) at a temperature of 170° C. for 5 minutes. The cooled reaction was diluted with methylene chloride and filtered through a small pad of silica gel. The filtrate was evaporated to dryness and purified via flash chromatography, eluting the pure C-acylated product 12 with CH2Cl2/hexanes (1:1). Pooled fractions were evaporated to afford 12 as a greenish yellow solid (0.388 g, 72% yield). 1H NMR (300 MHz, CDCl3): δ 2.69 (s, 3H, COCH3), 3.99 (s, 3H, OCH3), 6.84 (s, 1H, Ar-3-H), 7.80 (m, 2H, Ar—H), 8.10 (d, 1H, Ar—H), 8.21 (d, 1H, Ar—H), 13.76 (s, 1H, OH).

Workup

  1. customirradiated in the microwave reactor (Personal Chemistry, Inc) at a temperature of 170° C. for 5 minutes
  2. customThe cooled reaction
  3. filtrationfiltered through a small pad of silica gel
  4. customThe filtrate was evaporated to dryness
  5. custompurified via flash chromatography
  6. washeluting the pure C-acylated product 12 with CH2Cl2/hexanes (1:1)
  7. customPooled fractions were evaporated

Sources & evidence

ORD record
ord-df87a167d79b4d49aa105d583c2b33b2
Source dataset
uspto-grants-2008_02
Patent number
US07329687B2

Reaction notes

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