Hydrochloric Acid → HCID 13141992, compound

HRID 2418270Notes

Reaction equation

HRID 2418270 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([CH3:14])[CH2:12][Cl:13])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:15]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16].Cl>C(OCC)C>[C:15]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][C:1]([C:4]2[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([CH3:14])[CH2:12][Cl:13])=[CH:6][CH:5]=2)([OH:3])[CH3:2])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 88198Benzene, 1-(chloromethyl)-4-(1,1-dimethylethyl)-HCID 20446069HCID 20446069, compound

Product 1

HCID 13141992HCID 13141992, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

168.4 g of 3-(4-acetylphenyl)-2-methylpropyl chloride in 100 ml of diethyl ether were added dropwise to a Grignard suspension prepared from 182.5 g of 4-tert.-butylbenzyl chloride and 26 g of Mg in 400 ml of diethyl ether. After completion of the dropwise addition, the mixture was refluxed for a further 2 hours and then hydrolyzed by adding ice-cooled dilute aqueous HCl until the pH was 2. The organic products were extracted with ether, and the organic phase was washed with water, dried over Na2SO4 and concentrated. Distillation of the residue gave 163.4 g of (VI) of boiling point 190° C./0.1 mbar.

Workup

  1. additionAfter completion of the dropwise addition
  2. temperaturethe mixture was refluxed for a further 2 hours
  3. additionby adding ice-
  4. extractionThe organic products were extracted with ether
  5. washthe organic phase was washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-df0255595b53467caf372fdfe27a571a
Source dataset
uspto-grants-1984_09
Patent number
US04472412

Reaction notes

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