Acetic Acid → HCID 21864975, compound

HRID 856947Notes

Reaction equation

HRID 856947 reaction equation
C(O[C:4]1[C:11](C)=[CH:10][C:7]([CH:8]=O)=[C:6]([OH:13])[CH:5]=1)C.[C:14]([O-:17])(=[O:16])C.[Na+].C(O)(=O)C.[N+:23](CC)([O-])=O>>[OH:13][C:6]1[CH:5]=[CH:4][C:11]([O:16][CH2:14][OH:17])=[CH:10][C:7]=1[C:8]#[N:23]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6587NitroethaneHCID 517045Sodium AcetateHCID 21864978HCID 21864978, compound

Product 1

HCID 21864975HCID 21864975, compoundYield 61%

Conditions

Temperature
115 °C

Procedure

A mixture of 4-ethoxy-2-hydroxy-5-methyl-benzaldehyde (2.4 g, 14.6 mmol), sodium acetate (2.40 g, 29.25 mmol, 2.0 eq), acetic acid (3.4 g, 57.1 mmol, 3.9 eq), and nitroethane (2.2 g, 29.25 mmol, 2.0 eq) was heated in a sealed tube at 115° C. for 18 h. The black reaction mixture was poured into 40 g of ice and extracted 5 times with diethyl ether (100 mL). The organic layers were combined, washed 3 times with sat. sodium bicarbonate solution (25 mL), one time with brine, dried with sodium sulfate an finally concentrated in vacuo to give a black colored oil. Purification by MPLC chromatography (Biotage) using a hexane-ethyl acetate gradient gave 1.45 g (61%) of 2-hydroxy-5-hydroxymethoxy-benzonitrile as an orange solid. 1H-NMR (DMSO-d6) δ 10.69 (s, 1H), 7.04 (s, 1H), 6.51 (1, 2H), 6.01 (s, 2H); TLC Rf=0.73, 50% ethyl acetate-hexanes.

Workup

  1. customThe black reaction mixture
  2. extractionextracted 5 times with diethyl ether (100 mL)
  3. washwashed 3 times with sat. sodium bicarbonate solution (25 mL), one time with brine
  4. dry with materialdried with sodium sulfate
  5. concentrationan finally concentrated in vacuo
  6. customto give a black colored oil
  7. customPurification by MPLC chromatography (Biotage)

Sources & evidence

ORD record
ord-6125321bad9d482f8319d840d769a2b2
Source dataset
uspto-grants-2006_12
Patent number
US07144885B2

Reaction notes

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