Benzoic Acid → HCID 53995214, compound

HRID 1527816Notes

Reaction equation

HRID 1527816 reaction equation
[CH2:1]([C:3](=[CH:6][CH2:7][C@H:8]1[CH2:12][CH:11]=[C:10]([CH3:13])[C:9]1([CH3:15])[CH3:14])[CH:4]=[O:5])[CH3:2].C(O)(=O)C1C=CC=CC=1>>[CH2:1]([C:3](=[CH:6][CH2:7][C@H:8]1[CH2:12][CH:11]=[C:10]([CH3:13])[C:9]1([CH3:14])[CH3:15])[CH2:4][OH:5])[CH3:2]

Participants

3

Reactant 2

HCID 243Benzoic AcidHCID 57267566HCID 57267566, compound

Product 1

HCID 53995214HCID 53995214, compound

Conditions

Temperature
100 °C

Procedure

(R)-2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enal (as a 95/5 E/Z isomers mixture) (412 g, 2 mol.), benzoic acid (2.44 g, 0.02 mol., 1 mol.%) and (ethylenediamine)[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene]ruthenium(bispivalate) (37.6 mg, 0.04 mmol, 0.002 mol.%) were loaded altogether in a 1 L autoclave equipped with a mechanical stirring device. Sealed autoclave was then purged under stirring with nitrogen (3 times 5 bars) and hydrogen (3 times 5 bars) before being pressurized to 50 bars hydrogen. It was then heated to 100° C. and hydrogen pressure was maintained to 50 bars during all the reaction to afford desired product with 98.5% selectivity as a 95/5 E/Z isomers mixture and no loss of optical purity. Upon complete reaction conversion (checked by both hydrogen consumption and GC), autoclave was cooled down to 25° C. It was then depressurized and purged with nitrogen (3 times 5 bars). After flash distillation, (R)-2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol was obtained in 97.5% yield.

Workup

  1. customequipped with a mechanical stirring device
  2. customSealed autoclave
  3. customwas then purged
  4. temperaturehydrogen pressure was maintained to 50 bars during all
  5. customthe reaction

Sources & evidence

ORD record
ord-4d7addfca4ec43f19d0764e2206e2fc8
Source dataset
uspto-grants-2015_07
Patent number
US09090534B2

Reaction notes

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