Propofol → 2-(Chloromethoxy)-1,3-diisopropylbenzene

HRID 493057

Reaction equation

HRID 493057 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[OH:13])([CH3:3])[CH3:2].Br[CH2:15][Cl:16].[OH-].[Na+]>C1COCC1>[Cl:16][CH2:15][O:13][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 4943PropofolHCID 6333BromochloromethaneHCID 14798Sodium Hydroxide

Product 1

HCID 112531472-(Chloromethoxy)-1,3-diisopropylbenzeneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,6-diisopropylphenol was treated with bromochloromethane in the presence of sodium hydroxide and THF to give an 85% yield of O-chloromethyl-2,6-diisopropylphenol, which was purified by vacuum distillation. Treatment of O-chloromethyl-2,6-diisopropylphenol with phosphoric acid and triethylamine in acetonitrile followed by solvent removal, dissolution in methanol, pH adjustment and precipitation with acetone gave an 85% yield of phosphono-O-methyl 2,6-diisopropylphenol disodium salt.

Sources & evidence

ORD record
ord-1e7971a0d38a49eca606ccc4d2e6707b
Source dataset
uspto-grants-2009_05
Patent number
US07534776B2

Linked notes

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