Benzyl Alcohol → Benzyl 3-cyano-3-(4-hydroxyphenyl)propanoate

HRID 922254Notes

Reaction equation

HRID 922254 reaction equation
[C:1]([CH:3]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH2:4][C:5]([O:7][CH3:8])=[O:6])#[N:2].C(O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCC[Sn](O[Sn](CCCC)(CCCC)CCCC)(CCCC)CCCC>>[C:1]([CH:3]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH2:4][C:5]([O:7][CH2:8][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:6])#[N:2]

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 16682746Bis(tributyltin) oxideHCID 66685605Methyl 3-cyano-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 66685080Benzyl 3-cyano-3-(4-hydroxyphenyl)propanoateYield 6%

Procedure

To the microwave vial was charged with isomer methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (+ve) (0.5 g, 2.4 mmole) & benzyl alcohol (0.5 mL, 4.8 mmol), was added tributyltinoxide (0.03 g, 5% W/W). Temperature was set 90° C. & energy is fixed at 250 W for 30 mins. After completion of the reaction (monitored by TLC), the RM mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine solution, dried over anhydrous Na2SO4 and evaporated to dryness gave the titled compound (0.040 g, yield: 6.0%).

Workup

  1. customwas set 90° C.
  2. customAfter completion of the reaction (monitored by TLC)
  3. extractionthe RM mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine solution
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f5f9b0d2178840a68ee5d8ef459ee86a
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

Loading…