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Hydrochloric Acid → HCID 14726488, compound

HRID 1728465
Notes
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Reaction equation

HRID 1728465 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 mol) of dimethyl terephthalate and 23 g (0.1 mol) of 6-acetyl-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene in 80 ml of toluene and 20 ml of dimethoxyethane was added dropwise under nitrogen to a suspension of 3.6 g (0.15 mol) of sodium hydride in 21 ml of toluene at 100° C. The mixture was refluxed for 5 h and, after cooling, 50 ml of water were added, and the mixture was acidified with 50% concentrated hydrochloric acid, poured into 500 ml of water and extracted with chloroform. The precipitated product was filtered off with suction, and the chloroform phase was dried over sodium sulfate and concentrated. The residue and crude product were mixed and washed several times with hot methanol. Drying of the crystals resulted in 22.1 g of the title compound of melting point 128° C.

Workup

  1. temperatureThe mixture was refluxed for 5 h
  2. temperatureafter cooling
  3. extractionextracted with chloroform
  4. filtrationThe precipitated product was filtered off with suction
  5. dry with materialthe chloroform phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. additionThe residue and crude product were mixed
  8. washwashed several times with hot methanol
  9. customDrying of the crystals

Sources & evidence

ORD record
ord-fc6b59dc31a144f9b423e8e400c8a1f9
Source dataset
uspto-grants-1994_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05326900

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes