Isopropanol → Propan-2-yl 4-(chloromethyl)benzoate

Reaction equation

[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH:12](O)([CH3:14])[CH3:13]>>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH:12]([CH3:14])[CH3:13])=[O:8])=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 3776Isopropanol

HCID 742344-(Chloromethyl)benzoic acid

Product 1

HCID 20035448Propan-2-yl 4-(chloromethyl)benzoate

Procedure

Isopropyl 4-(chloromethyl)benzoate 13d was prepared by reacting 4-(chloromethyl)benzoic acid 24 with isopropanol according to the procedure described for the compound 13a in Example 16 (scheme 7). The benzoate 13d was isolated as colorless oil in 89% yield (1.90 g). 1H NMR (400 MHz, CDCl3): δ 1.35 (6H, m); 4.59 (2H, s); 5.25 (2H, m); 7.42 (1H, m); 7.44 (1H, broad s); 8.00 (1H, broad s); 8.02 (1H, s).

Workup

customIsopropyl 4-(chloromethyl)benzoate 13d was prepared

Sources & evidence

ORD record: ord-cf5dfa3f57074e74acc099ebb526e0c4
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247563B2

Reaction notes

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