Formaldehyde → HCID 12016846, compound

HRID 1062521Notes

Reaction equation

HRID 1062521 reaction equation
[C:1]12([C:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=3[OH:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([Mg]Br)C.[CH2:23]=[O:24].C(N(CC)CC)C>C1(C)C=CC=CC=1.CCOCC.C1COCC1>[C:1]12([C:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH:23]=[O:24])[C:12]=3[OH:18])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 6179922-(1-Adamantyl)-4-methylphenolHCID 178418443HCID 178418443, compound

Product 1

HCID 12016846HCID 12016846, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a 100 ml reactor thoroughly dried and purged with nitrogen, 11.22 g (46.30 mmol) of 2-(1-adamantyl)-4-methylphenol and 100 ml of THF were introduced. To the reactor, 16.20 ml of an ether solution containing 48.60 mmol of ethylmagnesium bromide was dropwise added at 0° C. over a period of 30 minutes, then the temperature of the system was slowly raised to room temperature, and the reaction solution was stirred at room temperature for 2.5 hours. Then, 300 ml of toluene was added, and the system was heated to 100° C. to give an opaque white slurry. After the slurry was cooled to room temperature, 3.80 g (126.54 mmol) of paraformaldehyde and 7.10 ml (70.17 mmol) of triethylamine were added, followed by stirring at 85° C. for 30 minutes. The reaction solution was allowed to cool to room temperature and then quenched with 10% hydrochloric acid. The organic layer was concentrated, and the solid precipitated was vacuum dried to obtain 10.51 g (yield: 84%) of 3-(1-adamantyl)-5-methylsalicylaldehyde.

Workup

  1. customInto a 100 ml reactor thoroughly dried
  2. additionwere introduced
  3. additionwas dropwise added at 0° C. over a period of 30 minutes
  4. temperaturethe system was heated to 100° C.
  5. customto give an opaque white slurry
  6. temperatureAfter the slurry was cooled to room temperature
  7. stirringby stirring at 85° C. for 30 minutes
  8. temperatureto cool to room temperature
  9. customquenched with 10% hydrochloric acid
  10. concentrationThe organic layer was concentrated
  11. customthe solid precipitated
  12. customdried

Sources & evidence

ORD record
ord-83e58dd33d554ddeae03d2c829323b83
Source dataset
uspto-grants-2005_11
Patent number
US06962890B2

Reaction notes

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