Water → HCID 22398278, compound

HRID 1070888Notes

Reaction equation

HRID 1070888 reaction equation
Br[C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH2:8][C:7]([CH3:15])([CH3:14])[C:6]=2[CH:5]=[C:4]([CH3:16])[C:3]=1[OH:17].C[O-].[Na+].[C:21](OCC)(=[O:23])C.O>CO>[CH3:21][O:23][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH2:8][C:7]([CH3:15])([CH3:14])[C:6]=2[CH:5]=[C:4]([CH3:16])[C:3]=1[OH:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 22398226HCID 22398226, compound

Product 1

HCID 22398278HCID 22398278, compoundYield 89.57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 1-Bromo-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenol (12.8 g, 43.06 mmol) and sodium methoxide in methanol (5.0M) was added CuBr (1.24 g, 8.61 mmol) followed by ethyl acetate (2.5 mL). The reaction was stirred and heated to reflux for 16 hours. The reaction mixture was cooled to room temperature then poured into water and extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and concentrated to yield 1-Methoxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenol (9.58 g, 89.57%). 1H NMR (CDCl3): δ 1.27 (s, 6H), 1.36 (s, 6H), 1.63-1.67 (m, 4H), 2.21 (s, 3H), 2.53 (s, 3H), 2.57 (s, 3H), 3.87 (s, 3H), 3.90 (s, 3H), 5.15 (d, 1H), 6.30 (s, 1H), 6.94 (s, 1H), 6.98 (s, 1H), 7.13 (d, 1H), 8.35 (s, 1H). APCI-MS m/z 532 (M+1).

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. extractionextracted with ethyl acetate
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-432e20104e7d4dbdadb907ca71899da4
Source dataset
uspto-grants-2005_06
Patent number
US06903132B2

Reaction notes

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