3-(Hydroxymethyl)benzophenone → 2,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

HRID 1762602Notes

Reaction equation

HRID 1762602 reaction equation
[CH3:1][C:2]1([CH3:16])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH2:11][CH3:12])=[O:8])[CH:3]1[C:13]([OH:15])=[O:14].C(C1C=C(CO)C=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:16][C:2]1([CH3:1])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH2:11][CH3:12])=[O:8])[CH:3]1[C:13]([OH:15])=[O:14].[CH3:1][C:2]1([CH3:16])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH3:10])=[O:8])[CH:3]1[C:13]([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 127837393-(Hydroxymethyl)benzophenoneHCID 545705842,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

Product 2

HCID 545705842,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acidHCID 867430702,2-Dimethyl-3-(3-methoxy-3-oxo-1-propeny)-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 9, (1R, cis, ΔZ) 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid and (3-benzoyl-phenyl)-methanol were reacted to obtain (3-benzoyl-phenyl)-methyl (1R, cis, Z) 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+52°±1.5° (c=1% in chloroform).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-8f504ac2d81c46adb6278a198b55e8b4
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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