Acetic Acid → Methyl 3,3-dicyclohexyl-2-hydroxy-3-methoxypropionate

HRID 729766Notes

Reaction equation

HRID 729766 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([OH:20])[C:5]([O:18][CH3:19])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)(=O)C>CO.O1CCOCC1>[CH:6]1([C:5]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)([O:18][CH3:19])[CH:4]([OH:20])[C:3]([O:2][CH3:1])=[O:21])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 10541193Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropanoate

Product 1

HCID 12073750Methyl 3,3-dicyclohexyl-2-hydroxy-3-methoxypropionateYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

10 g (34.9 mmol) of methyl-2-hydroxy-3-methoxy-3,3-diphenylpropionate were dissolved in 50 ml each of methanol and glacial acetic acid, 1 ml of RuO(OH)2 in dioxane was added, and hydrogenation was carried out with H2 in an autoclave at 100° C. under 100 bar for 30 h. The catalyst was filtered off, the mixture was concentrated, mixed with ether and washed with NaCl solution, and the organic phase was dried and concentrated. 10.1 g of methyl 3,3-dicyclohexyl-2-hydroxy-3-methoxypropionate were obtained as an oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe mixture was concentrated
  3. additionmixed with ether
  4. washwashed with NaCl solution
  5. customthe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0880d85ee76a4e8ba4cccb32a6ac9a38
Source dataset
uspto-grants-2009_09
Patent number
US07582647B2

Reaction notes

Loading…