Hydrochloric Acid → HCID 86750447, compound

HRID 975327Notes

Reaction equation

HRID 975327 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+].Br[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].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][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[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 84580Ethyl 5-bromovalerateHCID 144156666-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman

Product 1

HCID 86750447HCID 86750447, compoundYield 75%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolvent2×HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution containing 15.0 g (0.057 moles) of 6-acetoxy-3,4-dihydro-2-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran in 270 ml of benzene and 45 ml of dimethylsulfoxide is slowly dripped, under nitrogen atmosphere, into a suspension containing 1.98 g (0.080 moles) of 97% sodium hydride in 110 ml of dimethylsulfoxide. The reaction mixture, after 40 minutes, is slowly dripped into a solution containing 13.1 g (0.062 moles) of ethyl 5-bromovalerate in 80 ml of benzene and the mixture is reacted at 65° C. for 21 hours. The suspension is diluted with ethyl ether and water and acidified by means of a 10% aqueous solution of hydrochloric acid. The organic layer is filtered on a layer of silica 4 cm high and the product is recovered pure after elimination of the solvent and of the excess of reagents at the temperature of 170° C. and at the pressure of 2.0 millibar. The pure product under form of a thick oil, 16.76 g with yield of 75%, presents the following chemical-physical characteristics:

Workup

  1. customthe mixture is reacted at 65° C. for 21 hours
  2. filtrationThe organic layer is filtered on a layer of silica 4 cm high
  3. customthe product is recovered pure after elimination of the solvent
  4. customat the temperature of 170° C.

Sources & evidence

ORD record
ord-fc5486bc98574cfa81bea5073b4108e2
Source dataset
uspto-grants-1997_03
Patent number
US05608084

Reaction notes

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