Water → 3-Hydroxy-3-phenylbutyl 4-methylbenzenesulfonate

HRID 2037390Notes

Reaction equation

HRID 2037390 reaction equation
[C:1]1([C:7]([OH:12])([CH3:11])[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:20][C:19]1[CH:21]=[CH:22][C:16]([S:13]([O:10][CH2:9][CH2:8][C:7]([OH:12])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:11])(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 113240913-Phenylbutane-1,3-diol

Product 1

HCID 534742853-Hydroxy-3-phenylbutyl 4-methylbenzenesulfonateYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-phenylbutane-1,3-diol (68 g, 0.41 mol) in dry CH2Cl2 (500 mL) was added dropwise a solution of TsCl (78 g, 0.41 mol) and triethylamine (71 mL, 0.45 mol) in dry CH2Cl2 (500 mL) at 0° C. The mixture was stirred overnight. The mixture was poured into water and separated. The aqueous layer was extracted with CH2Cl2 (200 mL) twice. The organic layer was combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was purified by column chromatography to give 3-hydroxy-3-phenylbutyl 4-methylbenzenesulfonate (62 g, 42%). 1H NMR (400 MHz, CDCl3): δ=1.55 (s, 3H), 1.93 (w, 1H), 2.19˜2.24 (q, 2H), 2.45 (s, 3H), 3.87˜4.01 (m, 1H), 4.09˜4.16 (m, 1H), 7.19˜7.34 (m, 7H), 7.68˜7.76 (d, 2H).

Workup

  1. customseparated
  2. extractionThe aqueous layer was extracted with CH2Cl2 (200 mL) twice
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-9e6058db00304374b847f3c1836b51a6
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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