Hydrochloric Acid → HCID 53849019, compound

HRID 975325Notes

Reaction equation

HRID 975325 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:19])=[C:7]([CH3:18])[C:8]2[O:13][C:12]([OH:15])([CH3:14])[CH2:11][CH2:10][C:9]=2[C:16]=1[CH3:17])(=[O:3])[CH3:2].[H-].[Na+].[CH:22]([O:25][C:26](=[O:34])[C:27]([CH3:33])([CH3:32])[CH2:28][CH2:29][CH2:30]Br)([CH3:24])[CH3:23].Cl>C1C=CC=CC=1.CS(C)=O.C(OCC)C.O>[C:1]([O:4][C:5]1[C:6]([CH3:19])=[C:7]([CH3:18])[C:8]([O:13][CH2:30][CH2:29][CH2:28][C:27]([CH3:32])([CH3:33])[C:26]([O:25][CH:22]([CH3:23])[CH3:24])=[O:34])=[C:9]([CH2:10][CH2:11][C:12](=[O:15])[CH3:14])[C:16]=1[CH3:17])(=[O:3])[CH3:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 144156666-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchromanHCID 15688743HCID 15688743, compound

Product 1

HCID 53849019HCID 53849019, compoundYield 58%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolvent2×HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution containing 14.0 g (0.053 moles) of 6-acetoxy-3,4-dihydro-2-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran in 240 ml of benzene is added, by slow dripping and under nitrogen atmosphere, to a suspension containing 1.82 g (0.074 moles) of 97% sodium hydride in 100 ml of dimethylsulfoxide. After 40 minutes the solution is dripped into a solution containing 13.3 g (0.052 moles) of 2,2-dimethyl-5-bromopentanoic acid isopropyl ester in 60 ml of benzene and the mixture is reacted at 65° C. for 19 hours. The reaction mixture is then diluted with ethyl ether and water, acidified to pH 5 by means of a 10% aqueous solution of hydrochloric acid and the product is recovered pure by chromatography on silica gel column with eluent ethylene chloride-ethyl ether in 90:10 ratio. After evaporating the solvent an oil is obtained, 13.03 g with a yield of 58%, having the following chemical-physical characteristics:

Workup

  1. additionis added
  2. customthe mixture is reacted at 65° C. for 19 hours
  3. customthe product is recovered pure by chromatography on silica gel column with eluent ethylene chloride-ethyl ether in 90:10 ratio
  4. customAfter evaporating the solvent an oil
  5. customis obtained

Sources & evidence

ORD record
ord-aaea0038ccbd44fdb11e02a3feffa1cb
Source dataset
uspto-grants-1997_03
Patent number
US05608084

Reaction notes

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