Glycerol → 2,3-Dihydroxypropyl 4-(n-hexadecylamino)benzoate

HRID 1439282Notes

Reaction equation

HRID 1439282 reaction equation
[CH2:1]([NH:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)[CH2:2][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][CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:39][CH2:40][CH:41](CO)[OH:42]>>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH:41]([OH:42])[CH2:40][OH:39])=[O:23])=[CH:26][CH:27]=1)[CH2:2][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][CH3:16]

Participants

4

Reactant 3

HCID 753GlycerolHCID 6101p-Toluenesulfonic acidHCID 20437362HCID 20437362, compound

Product 1

HCID 130193802,3-Dihydroxypropyl 4-(n-hexadecylamino)benzoate

Conditions

Temperature
180 °C

Procedure

A mixture of 2.25 g of methyl 4-(n-hexadecylamino)benzoate, 280 mg of glycerol, 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 carbonate solution. The ether layer is separated, dried, and evaporated to yield 2,3-dihydroxypropyl 4-(n-hexadecylamino)benzoate.

Workup

  1. customis partitioned between ether and 3% aqueous carbonate solution
  2. customThe ether layer is separated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-65d2f090a0ed43cc9a7c1e5153f01d23
Source dataset
uspto-grants-1977_11
Patent number
US04058550

Reaction notes

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