Hydrochloric Acid → 2-Hydroxy-1-naphthalen-1-yl-propan-1-one

HRID 33573Notes

Reaction equation

HRID 33573 reaction equation
[C:1]1([CH:11]([O:15]C(=O)C)[C:12](=[O:14])[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:19][CH:20]([O:33]C(=O)C)[C:21]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)=[O:22].Cl>C(O)C>[OH:15][CH:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:12](=[O:14])[CH3:13].[OH:33][CH:20]([CH3:19])[C:21]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 51033133Acetic acid 1-naphthalen-1-yl-2-oxo-propyl esterHCID 597968292-Acetoxy-1-(naphth-1-yl)-1-propanone

Product 2

HCID 538227612-Hydroxy-1-naphthalen-1-yl-propan-1-oneYield 87%HCID 597968431-Hydroxy-1-naphthalen-1-yl-propan-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of acetic acid 1-naphthalen-1-yl-2-oxo-propyl ester and acetic acid 1-methyl-2-naphthalen-1-yl-2-oxo-ethyl ester (2:1 mixture) (16.7 g), ethanol (300 mL) and 1M hydrochloric acid (150 mL) was heated at reflux for 4 hours. After cooling to room temperature, the ethanol was removed under reduced pressure and the aqueous phase was extracted with dichloromethane (200 mL). The organic phase was washed with water (2×150 mL), brine (2×150 mL) dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford 1-hydroxy-1-naphthalen-1-yl-propan-2-one and 2-hydroxy-1-naphthalen-1-yl-propan-1-one (4:1 mixture) (12.0 g, 87%) as an orange oil, 1H NMR (DMSO-D6): 1.2 (3H, d, J=6.8 Hz), 2.0 (3H, s), 5.0 (1H, m), 5.35 (1H, d, J=6.5 Hz), 5.65 (1H, d, J=4.0 Hz), 6.15 (1H, d, J=4.0 Hz), 7.45-8.20 (10H, m).

Workup

  1. temperatureat reflux for 4 hours
  2. customthe ethanol was removed under reduced pressure
  3. extractionthe aqueous phase was extracted with dichloromethane (200 mL)
  4. washThe organic phase was washed with water (2×150 mL), brine (2×150 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7cd5b7048c4c4c709c2b562b42ec72bb
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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