Isopropanol → Methyl 3-chloro-4-isopropoxybenzoate

HRID 1820961Notes

Reaction equation

HRID 1820961 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[CH3:13][CH:14](O)[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:14]([CH3:15])[CH3:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 22597811Methyl 3-chloro-4-isopropoxybenzoateYield 101.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.42 g (7.63 mmol) of methyl 3-chloro-4-hydroxybenzoate, 585 μL (7.63 mmol) of 2-propanol and 3.0 g (11.45 mmol) of triphenylphosphine in 20 mL of THF at 0° C. was treated with 2.25 mL (11.45 mmol) of diisopropyl azodicarboxylate. The mixture was stirred for 16 h at rt, then concentrated. Chromatography on a Biotage 40M cartridge using 19:1 v/v hexanes/EtOAc as the eluant afforded 1.77 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.41 (d, J=6.2, 6H), 4.63-4.70 (m, 1H), 6.93 (d, J=8.7, 1H), 7.89 (dd, J=2.2, 8.6, 1H), 8.05 (d, J=2.0, 1H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-ba8958b1c8a9459d9ba22fbe5a037ec3
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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