Hydrochloric Acid → 4-(3-Hydroxypropyl)benzonitrile

HRID 704400Notes

Reaction equation

HRID 704400 reaction equation
[Li+].[B-](CC)(CC)CC.O1CCCC1.[C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](OC)=[O:25])=[CH:18][CH:17]=1)#[N:15].C(C1C=CC(C=O)=CC=1)#N.C1(P(=CC(OC)=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>O1CCCC1.O>[C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][OH:25])=[CH:18][CH:17]=1)#[N:15]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 660424-CyanobenzaldehydeHCID 14218717Methyl 3-(4-cyanophenyl)propanoateHCID 87145404Superhydride tetrahydrofuran

Product 1

HCID 110841784-(3-Hydroxypropyl)benzonitrileYield 67.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1M superhydride/tetrahydrofuran (3.3 ml) in anhydrous tetrahydrofuran (5 ml) was cooled to -50° to -60° C. under an argon gas stream. Thereto was added dropwise a solution of 210 mg of methyl 3-(4-cyanophenyl)propionate synthesized from 4-cyanobenzaldehyde and methyl (triphenylphosphoranylidene)acetate by the procedure of Reference Examples 69 and 76) in 2 ml of tetrahydrofuran. The resultant mixture was stirred at that temperature for 10 minutes, then made acidic by addition of water and 1N hydrochloric acid in that order at the same temperature, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 120 mg of 3-(4-cyanophenyl)propanol.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2cebdf18c874f788e572cf468ba9104
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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