Hydrochloric Acid → Ethyl 4-(4-chlorophenyl)-4-hydroxy-cyclohexanecarboxylate

HRID 1939882Notes

Reaction equation

HRID 1939882 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Cl)=[CH:4][CH:3]=1.[O:10]=[C:11]1[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1.Cl>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]2([OH:10])[CH2:12][CH2:13][CH:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 178478983HCID 178478983, compound

Product 1

HCID 21465094Ethyl 4-(4-chlorophenyl)-4-hydroxy-cyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Slowly add 4-chlorophenylmagnesium chloride (5.9 mL of 1M solution) to a solution of ethyl 4-oxo-cyclohexanecarboxylate (1.0 g) in Et2O at 0° C. After 1 h, pour the reaction mixture into 1N HCl and extract with Et2O. Separate the organic layer, wash with water, brine and concentrate to give ethyl 4-(4-chlorophenyl)-4-hydroxy-cyclohexanecarboxylate (1.75 g) which is used without purification in the next step.

Workup

  1. customat 0° C
  2. extractionextract with Et2O
  3. customSeparate the organic layer
  4. washwash with water, brine
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-10cab5fff31b41b083f636b97614c2d7
Source dataset
uspto-grants-1997_12
Patent number
US05698548

Reaction notes

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