Methyl 4-(chloromethyl)benzoate → 2-Phenyl-2,3-dihydrobenzo[1,4]oxathiin-6-ol

HRID 1455034Notes

Reaction equation

HRID 1455034 reaction equation
OC[CH:3]([S:10][C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:12]=1[OH:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:19]OC(=O)C1C=CC(CCl)=CC=1>C1(C)C=CC=CC=1>[C:9]1([CH:4]2[CH2:3][S:10][C:11]3[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:12]=3[O:18]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:19]=1

Participants

4

Reactant 2

HCID 36664Methyl 4-(chloromethyl)benzoateHCID 179785022-(2-Hydroxy-1-phenylethylsulfanyl)benzene-1,4-diol

Product 1

HCID 179784522-Phenyl-2,3-dihydrobenzo[1,4]oxathiin-6-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(2-hydroxy-1-phenylethylsulfanyl)benzene-1,4-diol (0.83 g) in dry toluene (60 ml) was stirred with Amberlyst 15 (0.5 g) at 60° C. until disappearance of the starting material. After the mixture was filtered and solvent evaporated the crude product was purified by column chromatography using heptane-ethyl acetate (1:1) as an eluant. 1H NMR (400 MHz, CDCl3) δ: 7.41 (m, 4H), 7.33-7.40 (m, 1H), 6.81 (d, 1H, J 8.7 Hz), 6.61 (d, 1H, J 3.0 Hz), 6.51 (dd, 1H, J 8.7, 3.0 Hz), 5.10 (dd, 1H, J 9.6, 1.9 Hz), 3.28 (dd, 1H, J 13.0, 9.6 Hz), 3.06 (dd, 1H, J 13.0, 1.9 Hz).

Workup

  1. filtrationAfter the mixture was filtered
  2. customsolvent evaporated the crude product
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-43ffdc08b3c84d42a92f629b97fc0c79
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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