Methyl Salicylate → 3-Hydroxy-2,2-bis(hydroxymethyl)propyl 2-hydroxybenzoate

HRID 477067Notes

Reaction equation

[C:1](OCC(CO)O)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH:16][CH2:17][C:18]([CH2:23][OH:24])([CH2:21][OH:22])[CH2:19][OH:20].C(OC)(=O)C1C(=CC=CC=1)O.C[O-].[Na+]>>[C:1]([O:16][CH2:17][C:18]([CH2:23][OH:24])([CH2:21][OH:22])[CH2:19][OH:20])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

Reactant 4

HCID 4133Methyl Salicylate2×

HCID 8285Pentaerythritol

HCID 38493182,3-Dihydroxypropyl salicylate

HCID 10942334Sodium Methoxide

Product 1

HCID 198373263-Hydroxy-2,2-bis(hydroxymethyl)propyl 2-hydroxybenzoate

Procedure

Pentaerythritol salicylate was prepared by the method described in Example 1 for the preparation of glycerol salicylate except that the reactants were pentaerythritol (34.04 g; 0.25 moles), methyl salicylate (86.72 g; 0.57 moles) and sodium methoxide (0.41 g; 0.0075 moles). The final methyl salicylate level was 12.5%.

Sources & evidence

ORD record: ord-929740d7afbb49628dcd4ca281163c70
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04886843

Reaction notes

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