Water → HCID 10192742, compound

HRID 1793203Notes

Reaction equation

HRID 1793203 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)=[C:4]([CH3:18])[C:3]=1[CH3:19].O>C1(C)C(C)=CC=CC=1>[CH3:19][C:3]1[C:2]([OH:1])=[CH:17][C:16]2[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:7][O:6][C:5]=2[C:4]=1[CH3:18]

Participants

4

Reactant 2

HCID 962WaterHCID 12112127HCID 12112127, compound

Product 1

HCID 10192742HCID 10192742, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(4-hydroxy-2,3-dimethyl-phenoxy)-1-phenyl-ethanone (1.2 g, 4.70 mmol) and polyphosphoric acid (ca. 100 mg) in xylene (10 mL) was stirred at 150° C. for 5 h. The mixture was poured into water, extracted with ethylacetate, washed and dried to give 6,7-dimethyl-3-phenyl-benzofuran-5-ol (560 mg) as a light brown solid. 1H NMR (CDCl3, 300 MHz) δ: 7.71 (s, 1H), 7.60–7.20 (m, 5H), 7.06 (s, 1H), 4.76 (s, 1H, OH), 2.47, 2.29 (2 s, 6H) ppm. 13C NMR (CDCl3, 75 MHz) δ: 150.43, 150.30, 141.15, 132.58, 129.00, 127.32, 123.48, 122.13, 121.31, 120.59, 102.25, 12.31, 11.95 ppm. MS (m/z): 239 (M+H+).

Workup

  1. extractionextracted with ethylacetate
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-c2ba31c2284e4a64a1f0849c2bdeeb97
Source dataset
uspto-grants-2006_07
Patent number
US07078541B2

Reaction notes

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