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1,3-Propanediol → 3-[3-(2,3-Dichlorophenylsulfonyloxy)-5-methylphenoxy]propanol

HRID 442907
Notes
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Reaction equation

HRID 442907 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)(=[O:11])=[O:10].C(P(CCCC)CCCC)CCC.[CH2:34](O)[CH2:35][CH2:36][OH:37].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[O:20][CH2:34][CH2:35][CH2:36][OH:37])(=[O:10])=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 109037243-(2,3-Dichlorophenylsulfonyloxy)-5-methylphenol

Product 1

HCID 537073253-[3-(2,3-Dichlorophenylsulfonyloxy)-5-methylphenoxy]propanolYield 91.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8058HexaneSolvent

Procedure

To a solution of 3-(2,3-dichlorophenylsulfonyloxy)-5-methylphenol (642 mg, 2.0 mnol), as prepared in the preceding step, tri-n-butylphosphine (607 mg, 3.0 mmol) and 1,3-propanediol (760 mg, 10 mmol) in anhydrous tetrahydrofuran (20 mL) was added 1,1'-(azodicarbonyl)dipiperidine (757 mg, 3.0 mmol). The mixture was stirred at ambient temperature overnight. Hexane (30 mL) was added to the mixture and the precipitates were removed by filtration. The filtrate was evaporated in vacuo, and the residue was purified by flash column chromatography (2:1 hexane/ethyl acetate) to give the title compound as a colorless oil (690 mg, 88%). 1H-NMR (300 MHz, CDCl3) δ 7.92 (d, J=8.0 Hz, 1 H), 7.76 (d, J=8.1 Hz, 1 H), 7.34 (t, J=8.0 Hz, 1 H), 6.62 (s, 1 H), 6.55 (s, 1 H),6.50(s, 1 H),4.02(t,J=6.0Hz,2H),3.82(t,J=5.7Hz,2H),2.26(s,3 H), 1.99 (m, 2 H), 1.58 (s, 1 H).

Workup

  1. customthe precipitates were removed by filtration
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was purified by flash column chromatography (2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d81e7c9d514f4994bc173bec437a25a1
Source dataset
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05891909

Reaction notes

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