Formaldehyde → HCID 87807692, compound

HRID 860972Notes

Reaction equation

HRID 860972 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH:20]([CH3:22])[CH3:21])[CH:14]=2)=[C:7]([Br:23])[CH:6]=1.C(N(CCCCCCCC)CCCCCCCC)CCCCCCC.[CH2:50]=[O:51]>Cl[Sn](Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:14]=[C:15]([CH:20]([CH3:22])[CH3:21])[C:16]([OH:19])=[C:17]([CH:50]=[O:51])[CH:18]=2)=[C:7]([Br:23])[CH:6]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 14227TrioctylamineHCID 69386373HCID 69386373, compound

Product 1

HCID 87807692HCID 87807692, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 24287Tin tetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

Methyl[3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)phenyl]acetate (2.0 g, 4.4 mmol), SnCl4 (25 μl, 0.2 mmol), trioctyl amine (0.77 mL, 1.76 mmol) and toluene (15 mL) were mixed in a reaction vial. After 20 minutes stirring at room temperature, paraformaldehyde (0.264 g, 8.8 mmol) was added to the reaction solution. The reaction vial was sealed and the temperature increased to 105° C. After 20 hours stirring, the reaction was quenched with ice-water and acidified with hydrochloric acid (1 N). Extraction with ethyl acetate, washing with brine, drying over Na2SO4 and concentration gave the crude product. The residue was purified on column (silica, gradient elution: n-heptane/ethyl acetate from 1:0 to 4:1) to give 1.08 g (51%) of methyl[3,5-dibromo-4-(3-formyl-4-hydroxy-5-isopropylphenoxy)phenyl]acetate.

Workup

  1. customThe reaction vial was sealed
  2. temperaturethe temperature increased to 105° C
  3. stirringAfter 20 hours stirring
  4. customthe reaction was quenched with ice-water
  5. extractionExtraction with ethyl acetate
  6. washwashing with brine
  7. dry with materialdrying over Na2SO4 and concentration
  8. customgave the crude product
  9. customThe residue was purified on column (silica, gradient elution: n-heptane/ethyl acetate from 1:0 to 4:1)

Sources & evidence

ORD record
ord-0fafe26dd9b84a41bd569cceb84f59b8
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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