p-Toluenesulfonic acid → 3-[1,3]Dioxan-2-yl-2'-methyl-biphenyl-4-ol

HRID 30611

Reaction equation

HRID 30611 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])=[CH:4][C:3]=1[CH:15]=[O:16].[OH:17][CH2:18][CH2:19][CH2:20]O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:16]1[CH2:20][CH2:19][CH2:18][O:17][CH:15]1[C:3]1[CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[CH:6]=[CH:7][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 200998674-Hydroxy-2'-methyl[1,1'-biphenyl]-3-carbaldehyde

Product 1

HCID 692176293-[1,3]Dioxan-2-yl-2'-methyl-biphenyl-4-olYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-hydroxy-2′-methyl-biphenyl-3-carbaldehyde (18.8 mmol) in toluene (100 mL) was added 1,3-dihydroxypropane (65.7 mmol) and p-toluenesulfonic acid (cat) and heated at reflux overnight in a Dean-Stark set-up. The reaction was cooled and washed with a solution of Na2CO3 (aq, 1 M). Evaporation in vacuo gave the title product as brown oil in 89% yield. 1H-NMR (CDCl3) δ 9.61 (bs, 1H), 7.34-7.10 (m, 6H), 6.87 (d, 1H), 5.77 (s,1H), 4.13-4.07 (m, 2H), 3.95-3.86 (m, 2H), 2.20 (s, 3H), 2.18-1.96 (m, 1H), 1.40 (d, 1H).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight in a Dean-Stark
  3. temperatureThe reaction was cooled
  4. washwashed with a solution of Na2CO3 (aq, 1 M)
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-12868647474649d7a47cf0fd64862070
Source dataset
uspto-grants-2008_09
Patent number
US07423181B2

Linked notes

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