Hydrochloric Acid → 1-Allyl-4-hydroxy-1-methylnaphthalen-2(1h)-one

HRID 494628Notes

Reaction equation

HRID 494628 reaction equation
[CH2:1]([C:4]1([CH3:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[CH:6]=[C:5]1[O:15]C)[CH:2]=[CH2:3].[OH-].[Na+].Cl>CO>[CH2:1]([C:4]1([CH3:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[CH:6][C:5]1=[O:15])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688739624-Allyl-3-methoxy-4-methylnaphthalen-1(4h)-one

Product 1

HCID 688712481-Allyl-4-hydroxy-1-methylnaphthalen-2(1h)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 123C (2.69 g, 11.8 mmol) in methanol (75 ml) was added a solution of 1N aqueous sodium hydroxide (75 mL) and the resultant mixture heated to reflux for 16 hours. After cooling to room temperature a solution of 1N aqueous hydrochloride (80 mL) was added to make the mixture acidic which caused a precipitate to form. This solid was collected by filtration, washed with water (5× 20 mL) and dried in a vacuum oven to provide the title compound as a light brown solid (1.97 g, 78%). 1H NMR (300 MHz, DMSO-d6): δ 1.44 (s, 3H), 2.65 (dd, J=13.2, 7.0 Hz, 1H), 2.80 (dd, J=13.6, 7.0 Hz, 1H), 4.72 (m, 2H), 5.08 (m, 1H), 5.66 (s, 1H), 7.36 (dt, J=7.2, 1.3 Hz, 1H), 7.56 (m, 1H), 7.65 (d, J=7.7 Hz, 1H), 7.89 (d, J=7.7 Hz, 1H).

Workup

  1. temperatureto reflux for 16 hours
  2. additionwas added
  3. customto form
  4. filtrationThis solid was collected by filtration
  5. washwashed with water (5× 20 mL)
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-6d412b92f26d4a47b5b3bfbbf1d7db0c
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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