Benzyl Bromide → 3-Benzyloxy-4-hydroxymethylbenzonitrile

HRID 378322Notes

Reaction equation

HRID 378322 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[OH:11])=[O:2].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].[BH4-].[Na+]>CO.C1COCC1>[CH2:12]([O:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[CH2:1][OH:2])[C:7]#[N:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 128136484-Formyl-3-hydroxybenzonitrile

Product 1

HCID 224760973-Benzyloxy-4-hydroxymethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

33.1 g of 4-formyl-3-hydroxybenzonitrile (Liebigs Ann. Chem. (1982) 1836) were O-benzylated with 1 eq. each of benzyl bromide and K2CO3 and, after workup, reduced with NaBH4 in 100 ml of MeOH/THF 2:3 at -10° C. to 0° C. to give the alcohol. 22.4 g were obtained. The product could be crystallized from DCM/petroleum ether. 1H-NMR (CDCl3, δ in ppm): 7.48 (1H), 7.40-7.3 (5H), 7.20 (1H), 7.08 (1H), 5.05 (s, 2H), 4.75 (s, 2H), 2.85 (1H, OH)

Sources & evidence

ORD record
ord-bbac5390e2a847cebf35acef6fb25343
Source dataset
uspto-grants-2000_02
Patent number
US06030972

Reaction notes

Loading…