Water → HCID 131712564, compound

HRID 1659307Notes

Reaction equation

HRID 1659307 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:14][C:13](O)([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6]1)[CH3:3].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:3][N:2]([CH2:4][CH:5]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6]1)[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 20560251HCID 20560251, compound

Product 1

HCID 131712564HCID 131712564, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-(N,N-dimethylaminomethyl)-4-hydroxy-4 (4'-chlorophenyl)-chroman (1.35 g) and tosic acid (10 mg) in benzene (75 ml) was heated under reflux with azeotropic removal of water for 31/2 hours. The solvent was removed under reduced pressure, the residue taken up in diethyl ether and washed with 2 N sodium hydroxide (20 ml). The organic phase was dried (MgSO4) and evaporated to give the title compound (1.08 g) as an oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with 2 N sodium hydroxide (20 ml)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-576a4665d1b74769aabdde20bf1eb6f7
Source dataset
uspto-grants-1981_12
Patent number
US04303656

Reaction notes

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