p-Toluenesulfonic acid → 3-Hydroxypropyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

HRID 652025Notes

Reaction equation

HRID 652025 reaction equation
[CH3:1][Si:2]([CH3:29])([CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1.C(O)[CH2:31][CH2:32][OH:33].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:29][Si:2]([CH3:1])([CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH2:31][CH2:32][OH:33])=[O:23])=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 20198250Methyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

Product 1

HCID 201982383-Hydroxypropyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

Procedure

A mixture of 2.2 g. of methyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate, 280 mg. of 1,3-propanediol and 1.37 g. of p-toluenesulfonic acid is heated at 180° C. for 18 hours and then is partitioned between ether and 3% aqueous sodium carbonate solution. The ether layer is separated, dried, and evaporated to yield the product as a white solid.

Workup

  1. additionA mixture of 2.2 g
  2. customis partitioned between ether and 3% aqueous sodium carbonate solution
  3. customThe ether layer is separated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-932668b7749347b1a028643aa6f6a0a1
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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