Hydrochloric Acid → HCID 22456878, compound

HRID 2186522Notes

Reaction equation

HRID 2186522 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[OH:17])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:18]I.Cl>[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([I:18])[C:16]=1[OH:17])[CH:12]=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 807IodineHCID 110206353-Benzyloxy-4-hydroxybenzaldehyde

Product 1

HCID 22456878HCID 22456878, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
77.5 °C

Procedure

To a mixture of 3-Benzyloxy-4-hydroxy benzaldehyde (15 g, 0.065 mol) and Iodine (17.54 g, 0.13 mol) was added 3.2% NaOH solution (150 ml). The reaction mixture was stirred at 75-80° C. for 8 h. The reaction mixture was cooled to room temperature and concentrated hydrochloric acid was added and the solid was filtered. Then the compound was recrystalized with isopropanol. The solid was filtered and dried to give 3-benzyloxy-4hydroxy-5-Iodo benzaldehyde (18.40 g, 79%). TLC: Ethyl acetate:light petroleum (2:5), Rf=0.4; 1H NMR (CDCl3, 200 MHz): δ 5.20 (s, 2H), 7.23-7.45 (m, 6H), 7.8 (d, J=1.42 Hz, 1H), 9.73 (s,1H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe solid was filtered
  3. customThen the compound was recrystalized with isopropanol
  4. filtrationThe solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-49dd88b67fa24c1d84d1dd696b377256
Source dataset
uspto-grants-2002_06
Patent number
US06403814B1

Reaction notes

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