Formaldehyde → HCID 19840938, compound

HRID 1638505Notes

Reaction equation

HRID 1638505 reaction equation
[CH3:1][C:2]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([OH:13])=[C:8]([CH:14]([CH3:16])[CH3:15])[CH:7]=1)([CH3:5])[CH2:3][CH3:4].C=O.S(=O)(=O)(O)O.[O:24]1[CH2:29]COC[CH2:25]1>>[CH3:5][C:2]([C:6]1[CH:7]=[C:8]([CH:14]([CH3:15])[CH3:16])[C:9]2[O:13][CH2:25][O:24][CH2:29][C:10]=2[C:11]=1[CH3:12])([CH3:1])[CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 19840936HCID 19840936, compound

Product 1

HCID 19840938HCID 19840938, compoundYield 35%

Procedure

Reaction of 4-(1,1-dimethylpropyl)-2-(1-methylethyl)-5-methylphenol (22.02 g, 0.1 mol), which may be prepared as described by W. Koenigs and R. W. Carl, Chem. Ber., (1981) 25, 3892-3903, 40% formaldehyde solution (70 mL, 0.93 mol), p-dioxane (150 mL) and sulfuric acid (10 mL) according to the procedure described in Example 2, provided after chromatography and short-path distillation, 9.18 g (35% yield) of 6-(1,1-dimethylpropyl)-5-methyl-8-(1-methylethyl)-4H-1,3-benzodioxin (GLC purity 98%); 1H-NMR (CDCl3)δ 0.70 (3H, t, J=7 HZ), 1.20 (6H, d, J=7 Hz), 1.35 (6H, s), 1.78 (2H, q, J=7 Hz), 2.15(3H, s), 3.0-3.5 (1H, m), 4.80 (2H, s), 5.17(2H, s), 7.03 (1H, s); IR (film) νmax 2950, 1575, 1470 cm-1 ; MS m/e 262, 233, 217, 203, 175, 161; UVλmax (ethanol) 226 nm (ε=5530), 283 nm (ε=1520).

Workup

  1. custommay be prepared
  2. customprovided

Sources & evidence

ORD record
ord-ef207f217a794ea5b18a01f3015387f8
Source dataset
uspto-grants-1989_11
Patent number
US04880775

Reaction notes

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