Sodium Hydroxide → 33382-06-8

HRID 1637800Notes

Reaction equation

HRID 1637800 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[O:11][CH2:10][C@H:9]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl.Cl[CH2:30][CH2:31][N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>C1(C)C=CC=CC=1.O>[CH3:19][O:18][C:14]1[CH:13]=[C:12]2[C:17]([C@H:8]([C:5]3[CH:4]=[CH:3][C:2]([O:1][CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:7][CH:6]=3)[C@H:9]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:10][O:11]2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 57180828HCID 57180828, compound

Product 1

HCID 21453333382-06-8

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

cis-4-(4-Hydroxyphenyl)-7-methoxy-3-phenylchromane (74.3 g) was dissolved in a mixture of toluene (700 ml), water (12 ml) and sodium hydroxide (24.3 g) by heating the mixture to 75° C. 2-Chloroethylpyrrolidin hydrochloride (46.2 g) was added in six portions at 75° C. with half an hour between each portion. After the last addition the mixture was heated at 75° C. for 4 hours. Water (1000 ml) was added and the mixture stirred until all salt was dissolved. The aqueous phase was separated and extracted with another portion of toluene (300 ml). The combined organic phases was dried over potassium carbonate and evaporated to an oil. The oil was dissolved in refluxing methanol (1000 ml) and the product crystallised by cooling in an ice bath.

Workup

  1. additionAfter the last addition the mixture
  2. temperaturewas heated at 75° C. for 4 hours
  3. dissolutionwas dissolved
  4. customThe aqueous phase was separated
  5. extractionextracted with another portion of toluene (300 ml)
  6. dry with materialThe combined organic phases was dried over potassium carbonate
  7. customevaporated to an oil
  8. dissolutionThe oil was dissolved
  9. temperaturein refluxing methanol (1000 ml)
  10. customthe product crystallised
  11. temperatureby cooling in an ice bath

Sources & evidence

ORD record
ord-919065d9d0da405093df174899899f2a
Source dataset
uspto-grants-2000_03
Patent number
US06043269

Reaction notes

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