Hydrochloric Acid → HCID 53703739, compound

HRID 648776Notes

Reaction equation

HRID 648776 reaction equation
[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[CH2:13][C:14](O)=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].Cl>C1(C)C=CC=CC=1>[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[CH2:13][CH2:14][OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 54424353HCID 54424353, compound

Product 1

HCID 53703739HCID 53703739, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred suspension of (cis-2-phenylcyclohexyl)acetic acid (15 g.) in dry toluene (100 ml.),cooled at -10° C. under argon, was treated with a 3.46 M solution of sodium bis(2-methoxyethoxy)aluminium hydride in toluene (25 ml.). The mixture was stirred overnight, diluted with ice/water (50 ml.), acidified with concentrated hydrochloric acid to pH 2. and extracted with ethyl acetate (3×150 ml.). The extracts were combined, washed with water (3×100 ml.), dried (MgSO4) and the solvent removed by evaporation to give 2-(cis-2-phenylcyclohexyl)ethanol (10.3 g.), which solidified on standing to give material of m.p. 48°-50° C.; NMR (CDCl3): 1.08-2.0 (12H,m), 2.81 (lH, d of t, Jaa=11 Hz, Jae=4 Hz, Jae=4 Hz, indicating cis-relative stereochemistry about the cyclohexane ring), 3.21 (1H,m), 3.37 (1H, m), 7.09 (3H,m), and 7.22 (2H,m).

Workup

  1. custom),cooled at -10° C. under argon
  2. extractionand extracted with ethyl acetate (3×150 ml.)
  3. washwashed with water (3×100 ml.)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-3200a0c1a9bc4b13ba2276483889275a
Source dataset
uspto-grants-1988_04
Patent number
US04736057

Reaction notes

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