Hydrochloric Acid → HCID 9817496, compound

HRID 1708151Notes

Reaction equation

HRID 1708151 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH2:21][N+:22]([O-:24])=O)[CH2:16][C:17](OC)=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Al].C1(C)C=CC=CC=1.Cl>O1CCCC1.O>[OH:24][N:22]1[CH2:21][CH:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:8]=2)[CH2:16][C:17]1=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 5359268AluminumHCID 18961181HCID 18961181, compound

Product 1

HCID 9817496HCID 9817496, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution containing 13.0 g (0.039 mol) methyl 3-(3-cyclopentyloxy-4-methoxyphenyl)-4-nitrobutanoate prepared above in 400 ml tetrahydrofuran containing 4 ml water was gradually added to 3.8 g aluminium foil treated before with a solution of mercuric chloride (1 g) in water. The temperature was held at 15°-20° C. by cooling. The mixture was stirred overnight at ambient temperature after which toluene and 200 ml 6N hydrochloric acid were added. The organic phase was separated and washed with 0.8M sodium hydrogen carbonate solution and evaporated to dryness in vacuo. The residue was crystallized from a mixture of dichloromethane-ether. Yield 1.7 g (15 mp 126°-130° C.

Workup

  1. customwas held at 15°-20° C.
  2. temperatureby cooling
  3. additionwere added
  4. customThe organic phase was separated
  5. washwashed with 0.8M sodium hydrogen carbonate solution
  6. customevaporated to dryness in vacuo
  7. customThe residue was crystallized from a mixture of dichloromethane-ether

Sources & evidence

ORD record
ord-afac0a0905eb419483a172e3c55983a8
Source dataset
uspto-grants-1994_10
Patent number
US05356923

Reaction notes

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