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

HRID 450964
Notes
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Reaction equation

HRID 450964 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent
2×

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-f216c40230ba45018c8ff71bb96a8f78
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08487094B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes