Hydrochloric Acid → 2-Hydroxy-5-nitrobenzyl alcohol

HRID 500424Notes

Reaction equation

HRID 500424 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+].Cl>[OH-].[Na+].CO>[OH:5][CH2:4][C:3]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=1[OH:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 668085-NitrosalicylaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 27638232-Hydroxy-5-nitrobenzyl alcoholYield 100.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-hydroxy-5-nitrobenzaldehyde (5.01 g, 30 mmol) in a mixture of 60 mL 1M NaOH and 30 mL MeOH was cooled to 0° C. NaBH4 (1.13 g, 30 mmol) solution in 15 mL 1M NaOH and 5 mL MeOH was added slowly. The reaction mixture was stirred for 24 hours at room temperature. The mixture was poured into ice cooled 2M HCl and extracted with EtOAc. The organic layer was washed, dried, and evaporated in vacuo to give the alcohol as a yellow solid (5.1 g, 100%): MP (112-114° C.); 1H NMR (DMSO-d6, 400 MHz) δ 11.08 (s, 1H), 8.18 (d, 1H, J=2.5 Hz), 8.00 (dd, 1H, J=2.5 and 8.7 Hz), 6.92 (d, 1H, J=8.8 Hz), 5.20 (br, 1H), 4.49 (s, 2H).

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-631d1ed3932a4f53a8f26132c2a55b07
Source dataset
uspto-grants-2010_08
Patent number
US07772216B2

Reaction notes

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