Ethanol → HCID 20379124, compound

HRID 2051598Notes

Reaction equation

HRID 2051598 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH2:5][CH3:6])[CH2:3][CH3:4].C(O)C>[Rh].C(O)(=O)C>[CH3:1][C:2]([CH:7]1[CH2:8][CH2:9][CH:10]([OH:13])[CH2:11][CH2:12]1)([CH2:5][CH3:6])[CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 702EthanolHCID 2235434-(3-methylpentan-3-yl)phenol

Product 1

HCID 20379124HCID 20379124, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of the 4-(3-methylpent-3-yl)phenol (365 g, 2.05 mol), ethanol (600 g), acetic acid (5.0 g) and 5% rhodium on carbon (8.0 g) was hydrogenated at 100 psi and 60° C. until the hydrogen absorption essentially ceased. The reaction mixture was filtered to remove the catalyst and the solvent was removed on a rotary evaporator. The resulting oil was washed with 10% sodium bicarbonate (200 ml) and then with water (200 ml portions) until a neutral pH (7) was indicated. Distillation of the crude oil under vacuum gave the desired 4-(3-methylpent-3-yl)cyclohexanol: 350 g, 93% yield; bp 110°-115° C. (2.0 mm); mol wt 184 (ms); nmr, 0.4-0.9 (9H, methyls), 1.0-1.5 (14H, m, CH2), 2.39 (1H, s, hydroxyl), 4.0 (1H, m, Hα to oxygen); ir, 3350, 2980, 2950, 2890, 1455, 1385, 1075, 1046, 960 cm-1.

Workup

  1. customwas hydrogenated at 100 psi and 60° C. until the hydrogen absorption
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. customthe solvent was removed on a rotary evaporator
  5. washThe resulting oil was washed with 10% sodium bicarbonate (200 ml)
  6. distillationDistillation of the crude oil under vacuum

Sources & evidence

ORD record
ord-f32bfd3825e94da591ee72cfe49ff3c6
Source dataset
uspto-grants-1980_01
Patent number
US04181631

Reaction notes

Loading…