Acetic Acid → HCID 131719077, compound

HRID 1756252Notes

Reaction equation

[CH2:1]([OH:23])[C@H:2]1[O:7][C@H:6]([O:8][C@:9]2([CH2:18][OH:19])[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@@H:10]2[OH:17])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].[C:24]([OH:27])(=[O:26])[CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:1]([OH:23])[C@H:2]1[O:7][C@H:6]([O:8][C@:9]2([CH2:18][OH:19])[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@@H:10]2[OH:17])[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].[C:24]([O-:27])(=[O:26])[CH3:25]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 5988Sucrose

HCID 6101p-Toluenesulfonic acid

HCID 10340Sodium Carbonate

Product 1

HCID 131719077HCID 131719077, compoundYield 95%

Conditions

Temperature: 100 °C

Procedure

Sucrose (34.2 g; 0.1 moles) can be mixed with acetic acid (50 g; 0.83 moles) and p-toluenesulfonic acid (0.2 g; 0.001 moles). The reaction mixture can then be heated to 100° C. for three hours. Sodium carbonate (0.1 g; 0.001 moles) can be added in order to neutralize the acid catalyst. Excess acetic acid can be removed at reduced pressure in a rotary evaporator. About 40 g of a partially esterified sucrose acetate (about 95 percent yield) containing about 70 weight percent sucrose diacetate and about 15 weight percent sucrose triacetate should be obtained.

Workup

customExcess acetic acid can be removed at reduced pressure in a rotary evaporator

Sources & evidence

ORD record: ord-3845ed03c4dd45f4ba7da911f3547a42
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05440027

Reaction notes

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