2-Bromopropane → 2-Isopropoxy-5-nonyl benzophenone

HRID 247228Notes

Reaction equation

HRID 247228 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[OH-].[Na+].[CH:27](Br)([CH3:29])[CH3:28].COC1C=CC(CCCCCCCCC)=CC=1C(C1C=CC=CC=1)=O>C(Cl)Cl.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:27]([O:1][C:2]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])([CH3:29])[CH3:28]

Participants

8

Reactant 4

HCID 63582-BromopropaneHCID 14798Sodium HydroxideHCID 93939Methanone, (2-hydroxy-5-nonylphenyl)phenyl-HCID 201619912-Methoxy-5-nonyl benzophenone

Product 1

HCID 201619762-Isopropoxy-5-nonyl benzophenone

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

2-Isopropoxy-5-nonyl benzophenone was prepared as follows. To 25 g of 2-hydroxy-5-nonyl benzophenone in 100 mL CH2Cl2 was added 20 g NaOH in 100 mL water, followed by the addition of 48 g isopropyl bromide and 2.5 g tetra-n-butyl-ammonium bromide. The entire mixture was stirred vigorously at 40° C. for 3 days. The reaction mixture was worked up as described for the preparation of 2-methoxy-5-nonyl benzophenone (Example II) to give 16 g of yellow oil (57% yield), identified as the desired product.

Sources & evidence

ORD record
ord-5c76ee7fd67f4b1bb7f26af43a3d66bf
Source dataset
uspto-grants-1987_11
Patent number
US04705896

Reaction notes

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