Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].N1C=CC=CC=1.[C:16](Cl)(=[O:18])[CH3:17].[Cl-].[NH4+]>C(Cl)Cl>[C:16]([O:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[OH:1])(=[O:18])[CH3:17]
Reactant: OCc1ccccc1O
Reactant: CC(=O)Cl
Agent: [Cl-]
Agent: [NH4+]
Solvent: c1ccncc1
Solvent: ClCCl
Product: CC(=O)OCc1ccccc1O
Reaction time: 0.5 h

Procedure:
2-Hydroxybenzyl alcohol (1.0 g) was dissolved in methylene chloride (20 ml), the solution was slowly added dropwise with pyridine (0.65 ml) and acetyl chloride (0.57 ml) under ice cooling, and the mixture was stirred for 30 minutes. The reaction mixture was added with saturated aqueous ammonium chloride, the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (1.22 g).