Hydrochloric Acid → HCID 19737029, compound

HRID 258214Notes

Reaction equation

HRID 258214 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([C:12]2([CH3:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[C:21]1([OH:27])C=CC=CC=1.C(Cl)(Cl)Cl.Cl>C(O)C.O>[C:1]([C:5]1[CH:10]=[C:9]([CH:21]=[O:27])[C:8]([OH:11])=[C:7]([C:12]2([CH3:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 996PhenolHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 19737032HCID 19737032, compound

Product 1

HCID 19737029HCID 19737029, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

4-t-butyl-2-(1-methylcyclohexyl)phenol (7.0 g, 0.028 mole) was dissolved in 10 ml of absolute ethanol in a 100 ml round bottom flask equipped with a water-cooled condenser. Sodium hydroxide (11.4 g, 0.28 mole) was dissolved in 10 ml water and added while still hot to the solution of phenol. Chloroform (6.8 g, 0.057 mole) was added in 2 to 3 ml portions over a 10-minute period. The resulting brown mixture was stirred for 1 hour while it cooled to ambient temperature. The mixture was added to 25 ml of 5M hydrochloric acid. The organic layer was isolated in a separatory funnel and dried over anhydrous magnesium sulfate. The mixture was filtered and rotoevaporated to a thick syrup to an assumed yield of 30% of the crude product with an IR spectrum having the characteristic aldehyde carbonyl stretching frequency. The product was used without further purification.

Workup

  1. temperaturecooled condenser
  2. customThe organic layer was isolated in a separatory funnel
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-3d4e6cc257a44361824675651229e5b9
Source dataset
uspto-grants-1993_11
Patent number
US05266283

Reaction notes

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