Ethyl Acetate → HCID 22000899, compound

HRID 1976304Notes

Reaction equation

HRID 1976304 reaction equation
C([O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([CH3:15])[CH:6]=1)(=O)C.[OH-].[Na+].CCOC(C)=O>O.CO>[CH3:15][C:7]1[CH:6]=[C:5]([OH:4])[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 22000894HCID 22000894, compound

Product 1

HCID 22000899HCID 22000899, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 5,6,7,8-tetrahydro-3-methyl-1-naphthyl acetate (11.00 g) and NaOH (6.50 g) in a mixture of water (50 ml) and MeOH (150 ml) was refluxed for 5 hours. MeOH was removed under reduced pressure to give a residue. AcOEt was added to the residue and c-HCl was added dropwise under ice-cooling. The organic phase was washed with brine and dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure to give 5,6,7,8-tetrahydro-3-methyl-1-naphthol as a solid (8.19 g).

Workup

  1. temperaturewas refluxed for 5 hours
  2. customMeOH was removed under reduced pressure
  3. customto give a residue
  4. additionwas added dropwise under ice-
  5. temperaturecooling
  6. washThe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-516ed98748574dd39effc3002b46913f
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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