Hydrochloric Acid → HCID 178443553, compound

HRID 2285871Notes

Reaction equation

HRID 2285871 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[Na].[H-].COCCO[Al+]OCCOC.[CH2:26]([C@H:33]1[CH2:38][CH2:37][C@H:36]([C:39]2[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=2)[CH2:35][CH2:34]1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].Cl>C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:26]([C@H:33]1[CH2:38][CH2:37][C@H:36]([C:39]2[CH:40]=[CH:41][C:42]([CH:43]=[O:44])=[CH:46][CH:47]=2)[CH2:35][CH2:34]1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[CH2:26]([C@H:33]1[CH2:38][CH2:37][C@H:36]([C:39]2[CH:40]=[CH:41][C:42]([CH2:43][OH:44])=[CH:46][CH:47]=2)[CH2:35][CH2:34]1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 16684438Red-AlHCID 86736934HCID 86736934, compoundHCID 178443556HCID 178443556, compound

Product 2

HCID 178443553HCID 178443553, compoundHCID 178443554HCID 178443554, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 1140TolueneSolvent

Procedure

Introduce 84 ml (0.3 mole) Vitride reducing agent (e.g. sodium-bis-(2-methoxy-ethoxy)aluminum hydride) and about 250 ml of dry benzene (or toluene) into 3-neck flask fitted with a condenser and air-stirrer and bring to reflux. Add dropwise in a course of 30 minutes a solution of 30 g trans-4(4-heptylcyclohexyl)benzoic acid in benzene and continue to reflux for additional 3-4 hours. Mixture is then cooled to room temperature and introduced slowly with stirring into a 20% aqueous HCl solution plus ice. After addition, the mixture is vigorously stirred for another 20 to 30 minutes and resulting layers are then separated. Evaporation of benzene yielded the desired compound, trans-4-(4-heptylcyclohexyl)benzylalcohol in typically 99.9% purity by gas chromatography and yields over 95%.

Workup

  1. customfitted with a condenser and air-stirrer
  2. temperatureto reflux
  3. temperatureto reflux for additional 3-4 hours
  4. additionintroduced slowly
  5. additionAfter addition
  6. customresulting layers
  7. customare then separated
  8. customEvaporation of benzene

Sources & evidence

ORD record
ord-fe6ae1368f8545f09a4609d3479ec064
Source dataset
uspto-grants-1982_04
Patent number
US04325830

Reaction notes

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