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Hydrochloric Acid → HCID 14726488, compound

HRID 346277
Notes
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Reaction equation

HRID 346277 reaction equation
[C:1]([O:13]C)(=O)[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:15]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24]([CH3:29])([CH3:28])[CH2:23][CH2:22][C:21]2([CH3:31])[CH3:30])(=[O:17])[CH3:16].[H-].[Na+].Cl>C1(C)C=CC=CC=1.C(COC)OC.O>[C:6]([C:5]1[CH:4]=[CH:3][C:2]([C:1](=[O:13])[CH2:16][C:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:24]([CH3:29])([CH3:28])[CH2:23][CH2:22][C:21]([CH3:31])([CH3:30])[C:20]=3[CH:19]=2)=[O:17])=[CH:11][CH:10]=1)([O:8][CH3:9])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8441Dimethyl terephthalateHCID 24758Sodium hydrideHCID 27475621-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

Product 1

HCID 14726488HCID 14726488, compoundYield 56.3%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
2×
HCID 1140TolueneSolvent2×
HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 19.4 g (0.1 mole) of dimethyl terephthalate and 23 g (0.1 mole) of 6-acetyl-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene in a mixture of 80 ml of toluene and 20 ml of dimethoxyethane was added dropwise at 100° C. to a suspension of 6.3 g (0.15 mole) of sodium hydride in 21 ml of toluene under nitrogen. The reaction mixture was refluxed with stirring for 5 hours and then cooled, after which 50 ml of water were added and the mixture was acidified with semiconcentrated hydrochloric acid, poured onto 500 ml of water and extracted with chloroform. The product which had already precipitated was filtered off under suction, and the chloroform phase was dried over sodium sulfate and evaporated down. The residue and the crude product filtered off under suction beforehand were combined and were extracted several times with hot methanol. After the remaining crystals had been dried, 22.1 g of 1-(4-carbomethoxyph-enyl)-3-(5,6,7,8-tetrahydro- 5,5,8,8-tetramethyl-2-naphthalenyl)-propane-1,3-dione of melting point 128° C. were obtained.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. temperaturecooled
  3. extractionextracted with chloroform
  4. customThe product which had already precipitated
  5. filtrationwas filtered off under suction
  6. dry with materialthe chloroform phase was dried over sodium sulfate
  7. customevaporated down
  8. filtrationThe residue and the crude product filtered off under suction beforehand
  9. extractionwere extracted several times with hot methanol
  10. customAfter the remaining crystals had been dried

Sources & evidence

ORD record
ord-68c0f88dc6944bfcbf2ad56e854b7716
Source dataset
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05061705

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes