Hydrochloric Acid → 1-(4-Methylcyclohexyl)propan-1-ol

HRID 2227565Notes

Reaction equation

HRID 2227565 reaction equation
[CH2:1]([Mg]Cl)[CH3:2].[CH3:5][CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]=[O:13])[CH2:8][CH2:7]1.[Cl-].[NH4+].Cl>O1CCCC1>[CH3:5][CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]([OH:13])[CH2:1][CH3:2])[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 138394374-Methylcyclohexane-1-carbaldehydeHCID 178461633HCID 178461633, compound

Product 1

HCID 184743551-(4-Methylcyclohexyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
22.5 °C

Procedure

180 ml (0.36 mol) of a 2 M ethylmagnesium chloride solution in tetrahydrofuran (THF) was first treated with a solution of 37.8 g (0.3 mol) of 4-methylcyclohexanecarbaldehyde (cis/trans) in 70 ml of THF and then stirred under protective gas atmosphere for approximately 16 hours at 20-25° C. After addition of 250 ml of 15% by weight ammonium chloride solution, the mixture was acidified with semiconcentrated hydrochloric acid and then extracted with methyl tert-butyl ether (MTBE). Washing of the combined organic phases with water and drying gave 44 g of 1-(4-methylcyclohexyl)propan-1-ol as a colorless oil. According to 1H NMR analysis, the ratio between the cis and trans isomers in the mixture amounted to approximately 35:65.

Workup

  1. extractionextracted with methyl tert-butyl ether (MTBE)
  2. washWashing of the combined organic phases with water
  3. customdrying

Sources & evidence

ORD record
ord-eb9482318c2849d7a8c967ec4962832b
Source dataset
uspto-grants-2002_07
Patent number
US06414031B1

Reaction notes

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