Sulfuric Acid → Ethyl 1-hydroxy-4,4-dimethyl-3-oxo-3,4-dihydro-2-naphthalenecarboxylate

HRID 1868792Notes

Reaction equation

HRID 1868792 reaction equation
OS(O)(=O)=O.[CH3:6][C:7]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:21])[C:8]([CH:10]([C:16]([O:18]CC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9]>CCOC(C)=O>[OH:18][C:16]1[C:23]2[C:22](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:7]([CH3:21])([CH3:6])[C:8](=[O:9])[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12369090Diethyl 2-(2-methyl-2-phenylpropanoyl)malonate

Product 1

HCID 57604805Ethyl 1-hydroxy-4,4-dimethyl-3-oxo-3,4-dihydro-2-naphthalenecarboxylateYield 57.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Concentrated H2SO4 (38.5 mL) was added dropwise via addition funnel to diethyl 2-(2-methyl-2-phenylpropanoyl)malonate (22.1 g, 72.1 mmol) cooled to 0° C. The reaction mixture was stirred for 2 hours at 0° C. and then poured into a flask containing ice, diluted with 400 mL of EtOAc, added to a separatory funnel, partitioned with water, washed 2 times with 100 mL of water, separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (10.82 g) as a white amorphous solid after flash chromatography. MS (m/z)=261 (M+H)+.

Workup

  1. additionpoured into a flask
  2. additioncontaining ice
  3. additionadded to a separatory funnel
  4. custompartitioned with water
  5. washwashed 2 times with 100 mL of water
  6. customseparated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-930e864aa0bf406ca8b4ec687690ec8b
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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