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Hydrochloric Acid → 4,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-one

HRID 1390
Notes
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Reaction equation

HRID 1390 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9](=[O:12])[C:8]2[CH:7]=[C:6](C(OC)=O)[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+].Cl>C(O)C.C1COCC1>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9](=[O:12])[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10681077Methyl 5,5-dimethyl-5,6 dihydro-naphthalen-8(7h)-one-2-carboxylate2×

Product 1

HCID 2365474,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of methyl-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate (Compound E2, 1.05 g, 4.5 mmol) in 10 mL of ethanol and THF (10 mL) was added sodiumhydroxide 9 mL (1M solution). The solution was stirred for 16 h and thereafter acidified with 10% HCl. The mixture was extracted with ethyl acetate, the combined organic layer was washed with water and brine, and dried over MgSO4. The solvent was distilled off under reduced pressure to afford the title compound as a white solid. 1H NMR (Acetone-D6): δ 1.44 (s, 6H), 2.07 (t, J=6.7 Hz, 2H), 2.73 (t, J=6.7 Hz, 2H), 7.70 (d, J=8.2 Hz, 1H), 8.19 (dd, J=1.9, 8.2 Hz, 1H), 8.57 (d, J=1.9 Hz, 1H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe combined organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5f9f7585dafc4f17ad29c89236ac8a9d
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723666

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes