Formaldehyde → HCID 86597176, compound

HRID 2108927Notes

Reaction equation

HRID 2108927 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]=O.[CH2:19](COC)[O:20]C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:19][OH:20])[C:12]([OH:15])=[C:11]([CH3:17])[C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 80711,2-DimethoxyethaneHCID 22625362HCID 22625362, compound

Product 1

HCID 86597176HCID 86597176, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To 684 mg (3 mmol) of 4-benzyloxy-3-methyl-phenol in 10 mL toluene and 1.5 mL DME (dimethoxyethane) in a sealable tube was added paraformaldehyde (1.8 g, 60 mmol). The tube was flushed with argon and sealed. It was heated to 130° C. for 48 h under stirring. After cooling to room temperature, the solid was filtered off and washed with 1:1 hexane/EtOAc and the liquid was concentrated. The residue was chromatographed to afford 4-benzyloxy-6-hydroxymethyl-2,3-dimethyl-phenol, as a light brown solid (640 mg). 1H-NMR (300 MHz, CDCl3/CD3OD)) δ (ppm): 7.43-7.29 (m, 5H), 6.55 (s, 1H), 4.95 (s, 2H), 4.70 (s, 2H), 2.18 (s, 3H), 2.16 (s, 3H); MS (ESI) m/z: 241 (M−OH−, 100%).

Workup

  1. customThe tube was flushed with argon
  2. customsealed
  3. temperatureAfter cooling to room temperature
  4. filtrationthe solid was filtered off
  5. washwashed with 1:1 hexane/EtOAc
  6. concentrationthe liquid was concentrated
  7. customThe residue was chromatographed

Sources & evidence

ORD record
ord-98b3dbea57b24f7c8105fbeb4ce0b3d1
Source dataset
uspto-grants-2009_04
Patent number
US07514461B2

Reaction notes

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