Water → HCID 22854878, compound

HRID 1647947Notes

Reaction equation

HRID 1647947 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[O:19])=[C:8]([Cl:20])[CH:7]=1)[CH3:5].B.[Na].O>CO>[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@@H:14]2[OH:19])=[C:8]([Cl:20])[CH:7]=1)[CH3:5].[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[OH:19])=[C:8]([Cl:20])[CH:7]=1)[CH3:5]

Participants

6

Reactant 3

HCID 962WaterHCID 15289641HCID 15289641, compoundHCID 178418435HCID 178418435, compound

Product 2

HCID 22854876HCID 22854876, compoundYield 30%HCID 22854878HCID 22854878, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6 g of methyl-2-[3-chloro-4-(2-oxocyclohexane-1-yl methyl)phenyl]propionate were dissolved in 30 ml of methanol and then incorporated with 0.75 g of sodium boron hydride under agitation at room temperature, agitated at room temperature for 30 minutes, incorporated with 100 ml of water and then extracted with 100 ml of ethyl acetate. The extract obtained was washed with water, dried and then freed of the solvent at a reduced pressure to obtain a mixture of trans-form and cis-form bodies. The thus obtained mixture was absorbed onto a silica gel-packed column and then separated with ethyl acetate-hexane (1:3) to obtain 1.8 g (yield 30%) of methyl-2-[3-chloro-4-(cis-2-hydroxycyclohexane-1-yl methyl)phenyl]propionate and 3.0 g (yield 50%) of methyl-2-[3-chloro-4-(trans-2-hydroxycyclohexane-1-yl methyl) phenyl]propionate.

Workup

  1. extractionextracted with 100 ml of ethyl acetate
  2. customThe extract obtained
  3. washwas washed with water
  4. customdried
  5. customto obtain
  6. additiona mixture of trans-form and cis-form bodies
  7. customThe thus obtained mixture was absorbed onto a silica gel-
  8. customseparated with ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-20dbc4d5032a4d0a9d90e1ace9aa5106
Source dataset
uspto-grants-1995_07
Patent number
US05434292

Reaction notes

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