Mesitylene → HCID 18701949, compound

HRID 278433Notes

Reaction equation

HRID 278433 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]CC=C)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1(C)[CH:24]=C(C)C=C(C)[CH:20]=1>>[CH2:24]([C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=[CH:13][C:12]=1[OH:15])[CH:19]=[CH2:20]

Participants

3

Reactant 2

HCID 7947MesityleneHCID 11128416HCID 11128416, compound

Product 1

HCID 18701949HCID 18701949, compoundYield 85%

Conditions

Temperature
165 °C

Procedure

1-Benzyloxy-4-allyloxy-benzene (20.4 g, 84.9 mmol) dissolved in mesitylene (150 ml) was heated at 165° C. for 48 hr under an argon atmosphere. After cooling to ambient temperature the resulting brown oil was chromatographed over SiO2 (Merck 230-400 mesh) eluting with EtOAc-nHexane (1:9) to afford 2-allyl-4-benzyloxy-phenol (17.45 g, 72.6 mmol, 85%) as a pale yellow oil MS m/e=240.1 (M+).

Workup

  1. temperatureAfter cooling to ambient temperature the resulting brown oil
  2. customwas chromatographed over SiO2 (Merck 230-400 mesh)
  3. washeluting with EtOAc-nHexane (1:9)

Sources & evidence

ORD record
ord-60a14b0a7db0446eb2f0f448657ce922
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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