4-Toluenesulfonyl chloride → HCID 178427753, compound

HRID 81089Notes

Reaction equation

HRID 81089 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C@H:12]1([CH2:20][OH:21])[CH2:17][CH2:16][C@H:15]([CH2:18][OH:19])[CH2:14][CH2:13]1.CCN(CC)CC>C(Cl)Cl>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:19][CH2:18][C@H:15]2[CH2:16][CH2:17][C@H:12]([CH2:20][OH:21])[CH2:13][CH2:14]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178520956HCID 178520956, compound

Product 1

HCID 178427753HCID 178427753, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Toluenesulfonyl chloride (742.5 g, 3.75 mol) was added to a solution of trans-cyclohexane-1,4-diyldimethanol (500 g, 4.17 mol) and Et3N (695 g, 5 mol) in DCM (6000 mL) at −20° C. The mixture was stirred at room temperature for 10 h and then quenched with water (10 L). The organic layer was separated, the aqueous layer was extracted with DCM (2×3 L), and the combined organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give trans-4-(hydroxymethyl)cyclohexylmethyl 4-methylbenzenesulfonate as a yellow oil.

Workup

  1. customquenched with water (10 L)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (2×3 L)
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-897e2997e61b482ab4b057fb6d14e464
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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