2-Methylbenzenesulfonic acid → HCID 24755527, compound

HRID 1159474Notes

Reaction equation

HRID 1159474 reaction equation
[OH:1][CH2:2][C:3]([CH3:13])([CH3:12])[CH2:4][NH:5][CH2:6][C:7]([CH3:11])([CH3:10])[CH2:8][OH:9].C(OCC)(OCC)(OCC)C.[C:25]1(C)[C:26](S(O)(=O)=O)=[CH:27]C=[CH:29][CH:30]=1>>[CH3:10][C:7]1([CH3:11])[CH2:6][N:5]2[C:29]([CH2:30][CH2:25][CH2:26][CH3:27])([O:1][CH2:2][C:3]([CH3:13])([CH3:12])[CH2:4]2)[O:9][CH2:8]1

Participants

4

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 66221Triethyl orthoacetateHCID 15055101HCID 15055101, compound

Product 1

HCID 24755527HCID 24755527, compound

Procedure

3-(3-Hydroxy-2,2-dimethyl-propylamino)-2,2-dimethyl-propan-1-ol (128.0 g, 0.68 mol), triethyl orthoacetate (162.0 g, 1.00 mol) and toluene sulfonic acid (2.0 g) were charged into a oven dried round bottom flask equipped with a stirring bar, distillation head and under nitrogen. The resulting solution was heated until the theoretical amount of methanol was collected. The reaction was cooled to room temperature and triethylamine added to neutralize the acid. Fractional vacuum distillations (twice) afforded the product as a water clear liquid, boiling point 101-103° C. at 0.44 torr. Yield: 156 g (90.5%).

Workup

  1. customdried round bottom flask
  2. customequipped with a stirring bar
  3. distillationdistillation head
  4. temperatureThe resulting solution was heated until the theoretical amount of methanol
  5. customwas collected
  6. additiontriethylamine added
  7. customFractional vacuum distillations (twice) afforded the product as a water clear liquid, boiling point 101-103° C. at 0.44 torr

Sources & evidence

ORD record
ord-9e6414aa04ca42a6a0001cc174cc7262
Source dataset
uspto-grants-2010_10
Patent number
US07812173B2

Reaction notes

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