Tert-butyl 2-chloro-4-(prop-1-en-2-yl)benzoate → HCID 89580719, compound

HRID 1479719Notes

Reaction equation

HRID 1479719 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([C:15]([CH3:17])=[CH2:16])[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]>CO.[Pt](=O)=O>[Cl:1][C:2]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

4

Reactant 1

HCID 89580914Tert-butyl 2-chloro-4-(prop-1-en-2-yl)benzoate

Product 1

HCID 89580719HCID 89580719, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 2-chloro-4-(prop-1-en-2-yl)benzoate (200 mg, 0.79 mmol) in methanol (20 mL) was added platinum(IV) oxide (20 mg). The resultant reaction mixture was stirred at room temperature for 24 hours under hydrogen atmosphere. Insoluble matters were removed using celite, and the filtrate was concentrated in vacuo to give tert-butyl 2-chloro-4-isopropylbenzoate (150 mg, 74.4%) as a white solid which was used in the next step directly. LRMS (M+H+) m/z: calcd 255.11. found 255 1H NMR (300 MHz, CD3OD) δ 7.67 (d, J=8.1 Hz, 1H), 7.36 (d, J=1.8 Hz, 1H), 7.28 (dd, J1=8.1 Hz, J2=1.8 Hz, 1H), 2.98 (m, 1H), 1.63 (s, 9H), 1.29 (d, J=6.9 Hz, 6H).

Workup

  1. customThe resultant reaction mixture
  2. customInsoluble matters were removed
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f2e76fdcdd37463688b14fcef61e5505
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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